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
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.
QUALITY CERTIFICATION / COMPLIANCE
Fukaya factory is certified for GMP, ISO14001:2004 (JQA-EM5386) and IQ Net (JP-JQA-EM5386).
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