Hydrazine hydrate (1:1) → (S)-2-((4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-yl)amino)propanehydrazide

HRID 1850131Notes

Reaction equation

HRID 1850131 reaction equation
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@@H:17]([CH3:22])[C:18](OC)=[O:19])[N:11]=1)([CH3:3])[CH3:2].O.[NH2:24][NH2:25]>>[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C@@H:17]([CH3:22])[C:18]([NH:24][NH2:25])=[O:19])[N:11]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86730166HCID 86730166, compound

Product 1

HCID 86730168(S)-2-((4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-yl)amino)propanehydrazideYield 78%

Procedure

To a solution of (S)-methyl 2-((4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-yl)amino)propanoate (120 mg, 0.39 mmol in 5 ml of MeOH) was added 99% hydrazine hydrate, the reaction solution was stirred at room temperature overnight (24 hours), the solvent was removed to yield the desired product (99 mg) in 78% yield, and was used for next step without purification. LCMS m/z 309.1 (M+H)+ RT=1.25 min.

Workup

  1. customthe solvent was removed

Sources & evidence

ORD record
ord-eb2bab16b08f4560b543cb4d78d8a189
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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