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

HRID 970784

반응식

HRID 970784 반응식
[O:1]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][O:18][C:19](=[O:31])[C@H:20]([N:28]=[C:29]=[O:30])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C1C=CN=CC=1>[CH3:17][O:18][C:19](=[O:31])[C@H:20]([NH:28][C:29]([O:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][CH:13]=1)=[O:30])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

참가 물질

4

반응물 2

HCID 6558897Methyl (R)-(+)-2-isocyanato-3-phenylpropionateHCID 11333367(4-(Phenoxymethyl)phenyl)methanol

생성물 1

HCID 12990904(R)-2-(4-Phenoxymethyl-benzyloxycarbonylamino)-3-phenyl-propionic Acid Methyl Ester수율 95.4%

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

실험 절차

(R)-Phenylalanine methyl ester hydrochloride (6.5 g, 30 mmol) was dissolved in methylene chloride and cooled to 0C. Phosgene (2M in toluene, 21.0 ml, 42.0 mmol) was added followed by pyridine (9.0 ml, 111 mmol). The mixture was allowed to warm to room temperature and was stirred for three hours. The mixture was then poured into dilute HCl. The layers were separated. The organic extracts were washed, dried, and concentrated to give about 5.8 g of a clear oil of (R)-2-isocyanato-3-phenyl-propionic acid methyl ester 5. 4-Phenoxymethylphenylmethanol 4 (0.857 g, 4.0 mmol), (R)-2-isocyanato-3-phenyl-propionic acid methyl ester 5 (1.026 g, 5.0 mmol) and 4-dimethylaminopyridine (DMAP) (10 mg) were combined, heated until molten, and stirred for 20 min. Upon cooling, the residue was purified by chromatography to give about 1.6 g of (R)-2-(4-phenoxymethyl-benzyloxycarbonylamino)-3-phenyl-propionic acid methyl ester 6.

후처리

  1. temperatureheated
  2. temperatureUpon cooling
  3. customthe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-0e6a776da3e0497d8c294e4f32ebdb61
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312230B2

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