Acetic Acid → tert-Butyl [(3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl]carbamate

HRID 1511452ノート

反応式

HRID 1511452 の反応式
[CH:1]1([N+:4]#[C-:5])[CH2:3][CH2:2]1.[O:6]=[CH:7][C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9][CH2:10][CH3:11].C(O)(=[O:22])C>C(Cl)Cl.C(OCC)(=O)C>[CH:1]1([NH:4][C:5](=[O:22])[CH:7]([OH:6])[C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9][CH2:10][CH3:11])[CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 176Acetic AcidHCID 2758008IsocyanocyclopropaneHCID 10262225Carbamic acid, [(1S)-1-formylbutyl]-, 1,1-dimethylethyl ester (9CI)

生成物 1

HCID 56604963tert-Butyl [(3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-yl]carbamate収率 88.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

To a solution of cyclopropylisonitrile (1.91 g, 28.5 mmol), (S)-tert-butyl 1-oxopentan-2-ylcarbamate (3.8 g, 19 mmol) in methylene chloride (100 mL) was added acetic acid (2.28 g, 38 mmol) at 0° C. After the addition was complete the reaction mixture was allowed to warm to 25° C. and stirred for 6 hours. The reaction mixture was diluted with ethyl acetate (200 mL), then washed with a saturated solution of sodium bicarbonate and brine (30 mL) and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the crude product was crystallized from 50 mL of ethyl acetate and hexane(v/v=1/1) to give tert-butyl (3S)-1-(cyclopropylamino)-2-hydroxy-1-oxohexan-3-ylcarbamate (4.8 g) as a white solid.

後処理

  1. additionAfter the addition
  2. washwashed with a saturated solution of sodium bicarbonate and brine (30 mL)
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe crude product was crystallized from 50 mL of ethyl acetate and hexane(v/v=1/1)

出典と根拠

ORDレコード
ord-8b8843b3851a4d78b8d746d1c3319784
出典データセット
uspto-grants-2012_07
特許番号
US08211897B2

反応ノート

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