Benzyl chloroformate → (2R,3S)-N-carbobenzyloxy-beta-phenyl isoserine methyl ester

HRID 1072942노트

반응식

HRID 1072942 반응식
[CH3:1][O:2][C:3](=[O:14])[C@H:4]([OH:13])[C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:6].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:14])[C@H:4]([OH:13])[C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH:6][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

참가 물질

6

반응물 2

HCID 10387Benzyl chloroformateHCID 10176516(2R,3S)-3-Phenylisoserine methyl ester

생성물 1

HCID 22865499(2R,3S)-N-carbobenzyloxy-beta-phenyl isoserine methyl ester

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of (2R,3S)-β-phenyl isoserine methyl ester (2) (Preparation No. 1, 2 mM) in pyridine containing a small amount of DMAP is cooled in an ice bath and treated with benzyl chloroformate (0.8 ml). After stirring at room temperature overnight, the reaction is diluted with ethyl acetate, washed with 5% aqueous sodium bisulfate, dried and evaporated. The product is obtained pure by silica gel chromatography in ethyl acetate-hexane mixtures. Mp 120-121° C. NMR(CDCl3, TMS): δ 3.26 (m, 1H); 3.79 (s, 3H); 4.47 (m, 1H); 5.06 (m, 2H); 5.27 (d, 1H); 5.75 (m, 1H); 7.20-7.50 (m, 10 H).

후처리

  1. washwashed with 5% aqueous sodium bisulfate
  2. customdried
  3. customevaporated
  4. customThe product is obtained pure by silica gel chromatography in ethyl acetate-hexane mixtures

출처 및 근거

ORD 기록
ord-2f9dbe92f7f1490f862f9fc257fd589a
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06911549B1

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