Hydrazine hydrate (1:1) → HCID 178451143, compound

HRID 1713830Notes

Reaction equation

HRID 1713830 reaction equation
O.[NH2:2][NH2:3].C[O:5][C:6](=O)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[CH2:21][CH2:20][C@H:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)=[O:8]>CCO>[NH:2]([C:6](=[O:5])[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[CH2:21][CH2:20][C@H:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)=[O:8])[NH2:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178501862HCID 178501862, compound

Product 1

HCID 178451143HCID 178451143, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Hydrazine hydrate (0.59 mL, 12.2 mmol) was added in one portion to a stirred mixture of tert-butyl trans-4-(4-{[methoxy(oxo)acetyl]amino}phenyl)cyclohexanecarboxylate (4.0 g, 11.1 mmol) in EtOH (50 mL) and the reaction mixture was stirred at room temperature for 3 h. EtOH (25 mL) was added and the mixture was filtered to give the title compound (Intermediate 79) (3.7 g, 92%) as a solid; 1H NMR δ 1.4 (9H, s), 1.4-1.5 (4H, m), 1.8-1.9 (2H, m), 1.9-2.0 (2H, m), 2.15-2.3 (1H, m), 2.4-2.55 (1H, m), 4.5 (1H, s), 4.6 (2H, s), 7.2 (2H, d), 7.7 (2H, d), 10.45 (1H, s); MS m/e (M−H)− 360.

Workup

  1. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-ab74efbe4f1f4f059d7da6ec45f0fcaa
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

Loading…