Ammonium Chloride → ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-hydroxyhexanoate

HRID 1173618ノート

反応式

HRID 1173618 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:21][CH3:22])[C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:21][CH3:22])[CH:13]([OH:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 67105603ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-oxohexanoate

生成物 1

HCID 67105208ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-hydroxyhexanoate収率 89%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
-78 °C

実験手順

To a solution of ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-oxohexanoate (70.68 g) in methanol (500 mL) was added sodium borohydride (9.66 g) at −78° C., and the mixture was stirred at −78° C. for 1 hr and at room temperature for 1 hr. Saturated aqueous ammonium chloride was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate) to give ethyl(4S)-4-{[(benzyloxy)carbonyl]amino}-3-hydroxyhexanoate (yield: 63.2 g, 89%) as a colorless solid.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

出典と根拠

ORDレコード
ord-b019ec1f5a9b47ebbf86724b6651cdaf
出典データセット
uspto-grants-2010_11
特許番号
US07834051B2

反応ノート

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