3,5-Difluorophenylacetic acid → HCID 86585288, compound

HRID 133296Notes

Reaction equation

HRID 133296 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.[NH2:14][C@H:15]([C:17]([C:19]1([NH2:44])[C:25](=[O:26])[N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:23]2[CH:33]=[CH:34][CH:35]=[CH:36][C:22]=2[N:21]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:20]1=[O:43])=[O:18])[CH3:16]>>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:14][C@H:15]([C:17]([C:19]2([NH2:44])[C:25](=[O:26])[N:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:23]3[CH:33]=[CH:34][CH:35]=[CH:36][C:22]=3[N:21]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:20]2=[O:43])=[O:18])[CH3:16])=[O:12])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 1454243,5-Difluorophenylacetic acidHCID 69037142HCID 69037142, compound

Product 1

HCID 86585288HCID 86585288, compound

Procedure

Following General Procedure I above using 3,5-difluorophenylacetic acid (Lancaster) and 3-(L-alaninyl)-amino-2,4-dioxo-1,5-bis-phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine hydrochloride (Example 8-W), the title compound was prepared as a white solid (melting point=139-141° C.). Purification was by flash chromatography eluting with CH2Cl2/EtOAc (1:1). Rf=0.46 (CH2Cl2/EtOAc, 1:1).

Workup

  1. customPurification
  2. washeluting with CH2Cl2/EtOAc (1:1)

Sources & evidence

ORD record
ord-ba927183e6e94644b6ab0b13ae128c9b
Source dataset
uspto-grants-2008_06
Patent number
US07390801B2

Reaction notes

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