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

HRID 1455585ノート

反応式

HRID 1455585 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(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+)

後処理

  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

出典と根拠

ORDレコード
ord-b7afdddfa58f4437b0799ef73b790418
出典データセット
uspto-grants-2009_01
特許番号
US07482448B2

反応ノート

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