Hydrazine hydrate (1:1) → HCID 69543759, compound

HRID 1278996Notes

Reaction equation

HRID 1278996 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:7][N:6]1[S:20]([C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)(=[O:22])=[O:21])=O.O.[NH2:34][NH2:35]>CO>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][S:10][C@H:8]2[CH2:7][N:6]([S:20]([C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=3)(=[O:22])=[O:21])[C@H:5]([C:3]([NH:34][NH2:35])=[O:2])[CH2:9]2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11374846HCID 11374846, compound

Product 1

HCID 69543759HCID 69543759, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(step 8) To a solution of 5 g (10.6 mmol, 1 eq) (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester in 20 ml methanol were added 6.45 ml (110 mmol, 10 eq) hydrazine-hydrate and the solution was stirred at RT for 3 days. The solvent was evaporated, followed by solving and evaporating with EtOH, ether and hexane. The light yellow solid was dried in vacuo giving (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid hydrazide, mp 130° C., MS: 472 (MH+).

Workup

  1. customThe solvent was evaporated
  2. customevaporating with EtOH, ether and hexane
  3. customThe light yellow solid was dried in vacuo

Sources & evidence

ORD record
ord-a60b12d0819d425fb6734151b54030c6
Source dataset
uspto-grants-2002_09
Patent number
US06444829B1

Reaction notes

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