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

HRID 133287Notes

Reaction equation

HRID 133287 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([F:13])[CH:12]=1)[CH:5]([OH:9])[C:6]([OH:8])=O.Cl.N[C@H](C([C:20]1([NH2:35])[C:26](=[O:27])[N:25]([CH3:28])[C:24]2[CH:29]=[CH:30][CH:31]=[CH:32][C:23]=2[N:22]([CH3:33])[C:21]1=[O:34])=O)C>>[F:13][C:11]1[CH:10]=[C:4]([CH:5]([OH:9])[C:6]([NH:35][C@H:20]([C:26]([NH:35][CH:20]2[C:21](=[O:34])[N:22]([CH3:33])[C:23]3[CH:32]=[CH:31][CH:30]=[CH:29][C:24]=3[N:25]([CH3:28])[C:26]2=[O:27])=[O:27])[CH3:21])=[O:8])[CH:3]=[C:2]([F:1])[CH:12]=1

Participants

3

Reactant 2

HCID 5886483,5-Difluoromandelic acidHCID 69033234HCID 69033234, compound

Product 1

HCID 229841283-[N'-(3,5-Difluorophenyl-a-hydroxyacetyl)-L-alaninyl]amino-2,4-dioxo-1,5-bis-methyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

Procedure

Following General Procedure I above using 3,5-difluoromandelic acid (Lancaster) and the product from Example 8-R, the title compound was prepared as an amorphous white solid. Purification was by L.C. 2000 eluting with straight EtOAc then flash chromatography eluting with CH2Cl2/Acetone (4:1 gradient to 3:1). Rf=0.39 and 0.34 (EtOAc).

Workup

  1. customPurification
  2. wash2000 eluting with straight EtOAc then flash chromatography eluting with CH2Cl2/Acetone (4:1 gradient to 3:1)

Sources & evidence

ORD record
ord-4f9337a7012647cbabe618e655802bdd
Source dataset
uspto-grants-2008_06
Patent number
US07390801B2

Reaction notes

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