3,5-Difluorophenylacetic acid → HCID 44344979, compound

HRID 2302282Notes

Reaction equation

HRID 2302282 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[CH:7]([NH:10][C:11](=[O:15])[C@@H:12]([NH2:14])[CH3:13])[C:6]2[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=2[C:4](=[O:20])[N:3]1[CH:21]([CH3:23])[CH3:22].[F:24][C:25]1[CH:26]=[C:27]([CH2:32][C:33](O)=[O:34])[CH:28]=[C:29]([F:31])[CH:30]=1>>[F:24][C:25]1[CH:26]=[C:27]([CH2:32][C:33]([NH:14][C@@H:12]([CH3:13])[C:11]([NH:10][CH:7]2[C:6]3[CH:16]=[CH:17][CH:18]=[CH:19][C:5]=3[C:4](=[O:20])[N:3]([CH:21]([CH3:23])[CH3:22])[N:2]([CH3:1])[C:8]2=[O:9])=[O:15])=[O:34])[CH:28]=[C:29]([F:31])[CH:30]=1

Participants

3

Reactant 2

HCID 1454243,5-Difluorophenylacetic acidHCID 12015736HCID 12015736, compound

Product 1

HCID 44344979HCID 44344979, compoundYield 75%

Procedure

In a manner similar to example 1, the title compound was prepared by the reaction of 2,3,4,5-tetrahydro-3-methyl-5(R,S)-[[(2S)-2-amino-1-oxopropyl]amino]-2-(1-methylethyl)-1H-2,3-benzodiazepin-1,4-dione with 3,5-difluorophenylacetic acid. The compound was purified on prep HPLC using the column YMC S5 ODS (20×100 mm) with a flow rate of 40 ml/min and gradient time of 10 min., starting with solvent A (10% MeOH—90% H2O—0.1% TFA), and ending with solvent B (90% MeOH—10% H2O—0.1% TFA). (75% yield). MS (ESI) 473.09 (M+H); Rf 1.31

Workup

  1. customThe compound was purified on prep HPLC
  2. customwith a flow rate of 40 ml/min and gradient time of 10 min.

Sources & evidence

ORD record
ord-22e63f0c94174f87bfb78bfe9a35d780
Source dataset
uspto-grants-2002_08
Patent number
US06432944B1

Reaction notes

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