Methyl (R)-(+)-2-isocyanato-3-phenylpropionate → (R)-2-(4-Phenethyloxybenzyloxycarbonylamino)-3-phenyl-propionic Acid Methyl Ester

HRID 970788Notes

Reaction equation

HRID 970788 reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:18][O:19][C:20](=[O:32])[C@H:21]([N:29]=[C:30]=[O:31])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C1C=CN=CC=1)C>[CH3:18][O:19][C:20](=[O:32])[C@H:21]([NH:29][C:30]([O:17][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([O:9][CH2:1][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:15][CH:14]=1)=[O:31])[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 6558897Methyl (R)-(+)-2-isocyanato-3-phenylpropionateHCID 12990905HCID 12990905, compound

Product 1

HCID 12990906(R)-2-(4-Phenethyloxybenzyloxycarbonylamino)-3-phenyl-propionic Acid Methyl EsterYield 96.9%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

(4-Phenethyloxyphenyl)methanol 11(1.141 g, 5.0 mmol), (R)-2-isocyanato-3-phenyl-propionic acid methyl ester 5 (1.036 g, 5.0 mmol) and DMAP (10 mg) were combined and heated until molten and stirred for 20 min. Upon cooling the residue was purified by chromatography to give about 2.1 g of (R)-2-(4-phenethyloxybenzyloxycarbonylamino)-3-phenyl-propionic acid methyl ester 12.

Workup

  1. temperatureheated
  2. temperatureUpon cooling the residue
  3. customwas purified by chromatography

Sources & evidence

ORD record
ord-ba77784cddc34f77b996690868be0c90
Source dataset
uspto-grants-2007_12
Patent number
US07312230B2

Reaction notes

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