Water → tert-butyl N-(3-{[(tert-butoxycarbonyl)sulfamoyl]amino}benzyl)-N-(trifluoroacetyl)glycinate

HRID 1497514노트

반응식

HRID 1497514 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]([C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C(N(CC)CC)C.Cl[S:32]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])(=[O:34])=[O:33].O>ClCCl>[C:38]([O:37][C:36]([NH:35][S:32]([NH:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]([C:15](=[O:20])[C:16]([F:17])([F:18])[F:19])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])(=[O:34])=[O:33])=[O:42])([CH3:41])([CH3:39])[CH3:40]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 15677406tert-butyl N-(chlorosulfonyl)carbamateHCID 90282000tert-butyl N-(3-aminobenzyl)-N-(trifluoroacetyl)glycinate

생성물 1

HCID 90282078tert-butyl N-(3-{[(tert-butoxycarbonyl)sulfamoyl]amino}benzyl)-N-(trifluoroacetyl)glycinate수율 73%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of tert-butyl N-(3-aminobenzyl)-N-(trifluoroacetyl)glycinate (1.95 g) and triethylamine (0.981 mL) in dichloromethane (19.5 mL) was added a solution of tert-butyl (chlorosulfonyl)carbamate (1.52 g) in dichloromethane (10.0 mL) under ice-cooling, followed by stirring at room temperature for 3 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue was added ethyl acetate, and n-hexane was added thereto. The precipitated solid was collected by filtration to obtain tert-butyl N-(3-{[(tert-butoxycarbonyl)sulfamoyl]amino}benzyl)-N-(trifluoroacetyl)glycinate (2.19 g).

후처리

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materiala saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue was added ethyl acetate, and n-hexane
  7. additionwas added
  8. filtrationThe precipitated solid was collected by filtration

출처 및 근거

ORD 기록
ord-ab444a29f427438982f56848eaefccda
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199927B2

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