APPLICATION
TCI Practical Example: Protection of Hydroxy Group Using BOM-Cl
Used Chemicals
Benzyloxymethyl Chloride (= BOM-Cl) [B1207]
Z-Ser-OMe [C1403]
N,N-Diisopropylethylamine (= DIEA) [D1599]
Dichloromethane
Procedure
DIEA (0.2 mL, 1.18 mmol, 1.5 eq.) and BOM-Cl (135 µL, 0.95 mmol, 1.2 eq.) were added to a solution of Z-Ser-OMe (200 mg, 0.79 mmol) in dichloromethane (3.9 mL) at room temperature. The reaction mixture was stirred for overnight. Additional DIEA (0.4 mL, 2.3 mmol, 3.0 eq.) and BOM-Cl (270 µL, 1.90 mmol, 2.4 eq.) were added and stirred for 8 h. The reaction mixture was quenched with sat. NaHCO3 aq. (5 mL) and extract with dichloromethane (3 x 5 mL), and washed with brine. Organic layer was dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate:hexane = 1:99 - 10:90 - 33:67 on silica gel), giving 1 as a colorless liquid (194 mg, 66% yield).
Experimenter’s Comments
The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:1, Rf = 0.68).
About 19% of Z-Ser-OMe was recovered.
Analytical Data
compound 1
1H NMR (270 MHz, CDCl3); δ 7.36-7.28 (m, 10H), 5.67 (brd, J = 8.4 Hz, 1H), 5.13 (s, 2H), 4.72 (s, 2H), 4.57 (m, 1H), 4.53 (s, 2 H), 4.12 (m, 1H), 3.81 (dd, J = 3.0, 10.0 Hz, 1H), 3.76 (s, 3H).
Other Reference
Effective and mild method for preparation of optically active α-amino aldehydes via TEMPO oxidation
J. Jurczak, D. Gryko, E. Kobrzycka, H. Gruza, P. Prokopowicz, Tetrahedron 1998, 54, 6051.
Application
BOM protection of Alcohols using Benzyloxymethyl Chloride
Protection
QUALITY CERTIFICATION / COMPLIANCE
Fukaya factory is certified for GMP, ISO14001:2004 (JQA-EM5386) and IQ Net (JP-JQA-EM5386).
PRECAUTIONARY STATEMENTS
P501 : Dispose of contents/ container to an approved waste disposal plant.
P261 : Avoid breathing dust/ fume/ gas/ mist/ vapors/ spray.
P270 : Do not eat, drink or smoke when using this product.
P210 : Keep away from heat/sparks/open flames/hot surfaces. No smoking.
P271 : Use only outdoors or in a well-ventilated area.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
P362 : Take off contaminated clothing and wash before reuse.
P301 + P312 + P330 : IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Rinse mouth.
P302 + P352 + P312 : IF ON SKIN: Wash with plenty of water.Call a POISON CENTER/doctor if you feel unwell.
P304 + P340 + P311 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Call a POISON CENTER/doctor.
P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.
P403 + P233 : Store in a well-ventilated place. Keep container tightly closed.
P403 + P235 : Store in a well-ventilated place. Keep cool.
P405 : Store locked up.
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