Hydrazine hydrate (1:1) → HCID 178471535, compound

HRID 1713872Notes

Reaction equation

HRID 1713872 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]([CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)=[O:8]>C(O)C>[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]([CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)=[O:8])[NH2:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178471537HCID 178471537, compound

Product 1

HCID 178471535HCID 178471535, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrate (229 mg, 4.57 mmol) was added in one portion to a stirred solution of trans-ethyl 2-[4-(4-{[methoxy(oxo)acetyl]amino}phenyl)cyclohexyl]propanoate (1.3 g, 3.6 mmol) in ethanol (25 mL) and the reaction mixture was stirred at room temperature for 18 h. The mixture was filtered to leave a solid, which was washed with ethanol (10 mL) to give the title compound (Intermediate 99) (1.2 g, 92%) as a solid; 1H NMR δ 1.07 (3H, d), 1.1-1.3 (2H, m), 1.2 (3H, t), 1.36-1.5 (2H, m), 1.5-1.63 (1H, m), 1.65-1.72 (1H, m), 1.75-1.88 (3H, m), 2.2-2.32 (1H, m), 2.35-2.49 (1H, m), 4.0-4.17 (2H, m), 4.6 (2H, s), 7.19 (2H, d), 7.7 (2H, d), 10.44 (1H, s); MS m/e MH+ 362.

Workup

  1. filtrationThe mixture was filtered
  2. customto leave a solid, which
  3. washwas washed with ethanol (10 mL)

Sources & evidence

ORD record
ord-1bf05206b3e94556ad60864cca9a8254
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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