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

HRID 411381Notes

Reaction equation

HRID 411381 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:13])[C:10]([OH:12])=O)[CH:5]=[C:6]([F:8])[CH:7]=1.[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:8][C:6]1[CH:5]=[C:4]([C:9](=[O:13])[C:10]([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:12])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 22312040(3,5-Difluorophenyl)glyoxylic acidHCID 235527623-(L-alaninyl)amino-2,3-dihydro-1-methyl-5-phenyl-1H-1,4-benzodiazepin-2-one

Product 1

HCID 229841333-[N'-(3,5-Difluorophenyl-alpha-oxoacetyl)-L-alaninyl]amino-2,3-dihydro-1-methyl-5-phenyl-1H-1,4-benzodiazepin-2-one

Procedure

Following General Procedure D above using 3,5-difluoro-α-oxoacetic acid (Example O) and 3-(L-alaninyl)amino-2,3-dihydro-1-methyl-5-phenyl-1H-1,4-benzodiazepin-2one (Example 8-B), the title compound was prepared as a solid (mp.=128-129° C.). The product was purified by LC 2000 chromatography, eluting with hexanes/ethyl acetate (30:70).

Workup

  1. customThe product was purified by LC 2000 chromatography
  2. washeluting with hexanes/ethyl acetate (30:70)

Sources & evidence

ORD record
ord-7845f4dbd5964786a72bf819c903dc2a
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Reaction notes

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