3,5-Difluorophenylacetic acid → 3-[N'-(3,5-Difluorophenylacetyl)-L-alaninyl]amino-2,4-dioxo-1,5-bis-methyl-2,3,4,5-tetrahydro-1-H-1,5-benzodiazepine

HRID 1369724Notes

Reaction equation

HRID 1369724 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[C:6]([F:8])[CH:7]=1.Cl.N[C@H](C([C:19]1([NH2:34])[C:25](=[O:26])[N:24]([CH3:27])[C:23]2[CH:28]=[CH:29][CH:30]=[CH:31][C:22]=2[N:21]([CH3:32])[C:20]1=[O:33])=O)C>>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:34][C@H:19]([C:25]([NH:34][CH:19]2[C:20](=[O:33])[N:21]([CH3:32])[C:22]3[CH:31]=[CH:30][CH:29]=[CH:28][C:23]=3[N:24]([CH3:27])[C:25]2=[O:26])=[O:26])[CH3:20])=[O:12])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 1454243,5-Difluorophenylacetic acidHCID 690332343-(L-alaninyl)-amino-2,4-dioxo-1,5-bis-methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine hydrochloride

Product 1

HCID 229840833-[N'-(3,5-Difluorophenylacetyl)-L-alaninyl]amino-2,4-dioxo-1,5-bis-methyl-2,3,4,5-tetrahydro-1-H-1,5-benzodiazepine

Procedure

Following General Procedure I above using 3,5-difluorophenylacetic acid (Lancaster) and 3-(L-alaninyl)-amino-2,4-dioxo-1,5-bis-methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine hydrochloride (Example 8-R), the title compound was prepared as a white solid (melting point=206-207° C.). Purification was by flash chromatography eluting with straight EtOAc gradient to EtOAc/Acetone (95:5). Rf=0.32 (EtOAc).

Workup

  1. customPurification
  2. washeluting with straight EtOAc gradient to EtOAc/Acetone (95:5)

Sources & evidence

ORD record
ord-223f3a979dcc43d9a569bfa262a1a53f
Source dataset
uspto-grants-2003_06
Patent number
US06579867B2

Reaction notes

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