3,5-Difluorophenylacetic acid → HCID 86585288, compound

HRID 411400Notes

Reaction equation

HRID 411400 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([NH:19][CH:20]1[C:26](=[O:27])[N:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:24]2[CH:34]=[CH:35][CH:36]=[CH:37][C:23]=2[N:22]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:21]1=[O:44])=O)C>>[F:8][C:6]1[CH:5]=[C:4]([CH2:9][C:10]([NH:19][C@H:20]([C:26]([C:20]2([NH2:19])[C:21](=[O:44])[N:22]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:23]3[CH:37]=[CH:36][CH:35]=[CH:34][C:24]=3[N:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:26]2=[O:27])=[O:27])[CH3:21])=[O:12])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 1454243,5-Difluorophenylacetic acidHCID 23552772HCID 23552772, 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-b952b0fd5cc14089aeb957dd76958503
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Reaction notes

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