2-(3,5-Difluorophenyl)-2-fluoroacetic acid → 3-[N'-(3,5-Difluorophenyl-alpha-fluoroacetyl)-L-alaninyl]amino-2,3-dihydro-1-methyl-5-phenyl-1H-1,4benzodiazepin-2-one

HRID 411385Notes

Reaction equation

HRID 411385 reaction equation
[F:1][CH:2]([C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]([F:13])[CH:7]=1)[C:3]([OH:5])=O.[NH2:14][C@H:15]([C:17]([NH:19][CH:20]1[N:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:24]2[CH:33]=[CH:34][CH:35]=[CH:36][C:23]=2[N:22]([CH3:37])[C:21]1=[O:38])=[O:18])[CH3:16]>>[F:13][C:8]1[CH:7]=[C:6]([CH:2]([F:1])[C:3]([NH:14][C@H:15]([C:17]([NH:19][CH:20]2[N:26]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:24]3[CH:33]=[CH:34][CH:35]=[CH:36][C:23]=3[N:22]([CH3:37])[C:21]2=[O:38])=[O:18])[CH3:16])=[O:5])[CH:11]=[C:10]([F:12])[CH:9]=1

Participants

3

Reactant 2

HCID 223127192-(3,5-Difluorophenyl)-2-fluoroacetic acidHCID 235527623-(L-alaninyl)amino-2,3-dihydro-1-methyl-5-phenyl-1H-1,4-benzodiazepin-2-one

Product 1

HCID 229841253-[N'-(3,5-Difluorophenyl-alpha-fluoroacetyl)-L-alaninyl]amino-2,3-dihydro-1-methyl-5-phenyl-1H-1,4benzodiazepin-2-one

Procedure

Following General Procedure D above using 3,5-difluorophenyl-α-fluoroacetic acid (Example S) and 3-(L-alaninyl)amino-2,3-dihydro-1-methyl-5-phenyl-1H-1,4-benzodiazepin-2-one (Example 8-Y), the title compound was prepared as a solid. The product was purified by LC 2000 chromatography, eluting with hexanes/ethyl acetate (35:65).

Workup

  1. customThe product was purified by LC 2000 chromatography
  2. washeluting with hexanes/ethyl acetate (35:65)

Sources & evidence

ORD record
ord-74f2abe92f6f413a84e4069f0853d912
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Reaction notes

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