Methyl chloroformate → (S)-benzyl 4-(difluoromethoxy)-2-(methoxycarbonylamino)butanoate

HRID 417662ノート

反応式

HRID 417662 の反応式
[NH2:1][C@@H:2]([CH2:13][CH2:14][O:15][CH:16]([F:18])[F:17])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[CH3:19][O:20][C:21](Cl)=[O:22]>ClCCl>[F:18][CH:16]([F:17])[O:15][CH2:14][CH2:13][C@H:2]([NH:1][C:21]([O:20][CH3:19])=[O:22])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]

参加物

4

反応物 2

HCID 6586Methyl chloroformateHCID 67991507(S)-benzyl 2-amino-4-(difluoromethoxy)butanoate

生成物 1

HCID 59610623(S)-benzyl 4-(difluoromethoxy)-2-(methoxycarbonylamino)butanoate収率 40%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

(S)-Benzyl 2-amino-4-(difluoromethoxy)butanoate (116 mg, 0.448 mmol) was dissolved in anhydrous dichloromethane (2.5 mL) and cooled down to 0° C. and TEA (181 mg, 1.79 mmol) and methylchloroformate (51 mg, 0.538 mmol) were added respectively. The mixture was stirred for 30 minutes and then it was stirred at room temperature overnight. The resulting product mixture was quenched with saturated NaHCO3 and extracted with dichloromethane. The organic layer was washed with saturated NH4Cl solution and brine and dried over Na2SO4. The volatiles were removed in vacuo to afford 56 mg (40%) of desired product after column purification.

後処理

  1. stirringit was stirred at room temperature overnight
  2. customThe resulting product mixture was quenched with saturated NaHCO3
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with saturated NH4Cl solution and brine
  5. dry with materialdried over Na2SO4
  6. customThe volatiles were removed in vacuo

出典と根拠

ORDレコード
ord-62b426d4febe4ea68f6f2a9766510c94
出典データセット
uspto-grants-2012_01
特許番号
US08088368B2

反応ノート

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