Allyl chloroformate → HCID 57587980, compound

HRID 1782045Notes

Reaction equation

HRID 1782045 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][NH:6][CH:7]([C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].C(N(C(C)C)C(C)C)C.Cl[C:32]([O:34][CH2:35][CH:36]=[CH2:37])=[O:33]>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][N:6]([C:32]([O:34][CH2:35][CH:36]=[CH2:37])=[O:33])[CH:7]([C:14]1[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 18052Allyl chloroformateHCID 81531DiisopropylethylamineHCID 57587999HCID 57587999, compound

Product 1

HCID 57587980HCID 57587980, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

(RS)-{[(4-Chloro-phenyl)-phenyl-methyl]-amino}-acetic acid ethyl ester (18 g, 59 mmol) was dissolved under nitrogen in DCM (1500 mL), N-ethyldiisopropylamine (12.2 mL, 71 mmol) was added, cooled in ice and treated with a solution of allyl chloroformate (6.4 mL, 71 mmol) in DCM (50 mL). Stirring at 20° C. was continued for 16 h. The solution was extracted with 1 M citric acid (200 mL) and 50% NaCl solution. The crude product was purified by chromatography on silica gel in heptane with a gradient of ethyl acetate from 0-50% in 60 min. One obtained 18.1 g (78%) of colorless oil. MS: m/z=388 [M+H]+.

Workup

  1. temperaturecooled in ice
  2. extractionThe solution was extracted with 1 M citric acid (200 mL) and 50% NaCl solution
  3. customThe crude product was purified by chromatography on silica gel in heptane with a gradient of ethyl acetate from 0-50% in 60 min

Sources & evidence

ORD record
ord-bf91387b33b445feb8e3e4035c5d2fe0
Source dataset
uspto-grants-2009_03
Patent number
US07498339B2

Reaction notes

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