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

HRID 1072942ノート

反応式

HRID 1072942 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2f9dbe92f7f1490f862f9fc257fd589a
出典データセット
uspto-grants-2005_06
特許番号
US06911549B1

反応ノート

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