Acetic Acid → tert-butyl N-[(2S)-1-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropan-2-yl]carbamate

HRID 1994125ノート

反応式

HRID 1994125 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[Li+].[BH4-].[Na+].C(O)(=O)C>C1COCC1.C(O)C>[OH:11][CH2:10][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:14][NH:15][C:16](=[O:17])[O:18][C:19]([CH3:21])([CH3:22])[CH3:20]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 86606495HCID 86606495、化合物

生成物 1

HCID 86606496tert-butyl N-[(2S)-1-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropan-2-yl]carbamate収率 72.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl (2S)-2,3-bis[(tert-butoxycarbonyl)amino]-propanoate (3.57 g, 11.2 mmol) in THF (60 mL) at 0° C. was added lithium chloride (523 mg, 12.3 mmol) and then sodium borohydride (467 mg, 12.3 mmol) portionwise. Ethanol (30 mL) was added slowly. The reaction mixture was allowed to warm to rt and stirred for 18 h. Acetic acid (0.707 mL, 12.3 mmol) was added and the solvents were evaporated. The residue was purified by chromatography (SiO2, EtOAc/hexane) to yield the title compound as a white solid (2.35 g, 72.2%). LCMS: (FA) ES+ 291.2 (M+1).

後処理

  1. customthe solvents were evaporated
  2. customThe residue was purified by chromatography (SiO2, EtOAc/hexane)

出典と根拠

ORDレコード
ord-1c06efc9f3db4ec1a0d2f702ec34232f
出典データセット
uspto-grants-2010_01
特許番号
US07652041B2

反応ノート

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