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

HRID 1455585Notes

Reaction equation

HRID 1455585 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(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+)

Workup

  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

Sources & evidence

ORD record
ord-b7afdddfa58f4437b0799ef73b790418
Source dataset
uspto-grants-2009_01
Patent number
US07482448B2

Reaction notes

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