4-(Trifluoromethoxy)benzoic acid hydrazide → Acetic acid (s)-2-tert-butoxycarbonylamino-1-[n'-(4-trifluoromethoxy-benzoyl)hydrazinocarbonyl]-butyl ester

HRID 1455585노트

반응식

HRID 1455585 반응식
[C:1]([O:4][C@@H:5]([CH:9]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH3:11])[C:6]([OH:8])=O)(=[O:3])[CH3:2].[F:20][C:21]([F:34])([F:33])[O:22][C:23]1[CH:32]=[CH:31][C:26]([C:27]([NH:29][NH2:30])=[O:28])=[CH:25][CH:24]=1>ClCCl>[C:16]([O:15][C:13]([NH:12][CH:9]([CH2:10][CH3:11])[C@H:5]([O:4][C:1](=[O:3])[CH3:2])[C:6]([NH:30][NH:29][C:27](=[O:28])[C:26]1[CH:25]=[CH:24][C:23]([O:22][C:21]([F:20])([F:34])[F:33])=[CH:32][CH:31]=1)=[O:8])=[O:14])([CH3:19])([CH3:18])[CH3:17]

참가 물질

4

반응물 2

HCID 27772304-(Trifluoromethoxy)benzoic acid hydrazideHCID 87587800(s)-2-Acetoxy-3-tert-butoxycarbonylamino-pentanoic acid

생성물 1

HCID 86607346Acetic acid (s)-2-tert-butoxycarbonylamino-1-[n'-(4-trifluoromethoxy-benzoyl)hydrazinocarbonyl]-butyl ester수율 64%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(S)-2-acetoxy-3-tert-butoxycarbonylamino-pentanoic acid (1.82 mmol, 0.5 g, A) is dissolved in 30 mL dichloromethane. N-Cyclohexylcarbodiimide-N′-methylpolystyrene (3.64 mmol, 1.92 g, B) is added and the resulting reaction mixture stirred for 2 min. 4-(trifluoromethoxy)benzoic acid hydrazide (1.65 mmol, 0.363 g, C) is added and the reaction mixture stirred over night. After 16 hours LC/MS analysis still showed hydrazide. Polystyrene methyl isocyanate (1.65 mmol, 1.15 g) is added and stirring continued for eight hours. The reaction mixture is filtered under suction and the filtrate concentrated under reduced pressure. To give acetic acid (S)-2-tert-butoxycarbonylamino-1-[N′-(4-trifluoromethoxy-benzoyl)hydrazinocarbonyl]-butyl ester as a foam (0.5 g, 64%). According to LC/MS still some hydrazide present. MS: m/z=500 (M+Na+), 478 (M+H+)

후처리

  1. customthe resulting reaction mixture
  2. stirringthe reaction mixture stirred over night
  3. stirringstirring
  4. waitcontinued for eight hours
  5. filtrationThe reaction mixture is filtered under suction
  6. concentrationthe filtrate concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b7afdddfa58f4437b0799ef73b790418
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482448B2

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