Hydrazine hydrate (1:1) → HCID 59608162, compound

HRID 2384113Notes

Reaction equation

HRID 2384113 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:17][C:18](=[O:24])[C:19]([O:21]CC)=O)[CH2:9][C@@H:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:3][CH:2]=1.O.[NH2:32][NH2:33]>CO>[C:1]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@@H:8]([NH:17][C:18](=[O:24])[C:19]([NH:32][NH2:33])=[O:21])[CH2:9][C@@H:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59608173HCID 59608173, compound

Product 1

HCID 59608162HCID 59608162, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of (2R,4S)-ethyl 5-(biphenyl-4-yl)-4-(2-ethoxy-2-oxoacetamido)-2-methylpentanoate (970 mg, 2.34 mmol) in anhydrous MeOH (20 mL) cooled to −20 deg C. is added a solution of 50% wt hydrazine hydrate (0.15 mL, 2.36 mmol) in MeOH (10 mL) dropwise. The crude is allowed to warm to rt in 2 hrs and is stirred overnight. The crude white precipitate is filtered to give (2R,4S)-ethyl 5-(biphenyl-4-yl)-4-(2-hydrazinyl-2-oxoacetamido)-2-methylpentanoate (870 mg). HPLC retention time=1.70 minutes (condition A); MS 398.2 (M+1).

Workup

  1. filtrationThe crude white precipitate is filtered

Sources & evidence

ORD record
ord-99d4752a381048438414e95040d3739a
Source dataset
uspto-grants-2012_09
Patent number
US08263629B2

Reaction notes

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