3,5-Difluorophenylacetic acid → HCID 86584979, compound

HRID 411396Notes

Reaction equation

HRID 411396 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([NH2:42])[C:25](=[O:26])[N:24]([CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[C:23]2[CH:32]=[CH:33][CH:34]=[CH:35][C:22]=2[N:21]([CH2:36][C:37]([CH3:40])([CH3:39])[CH3:38])[C:20]1=[O:41])=[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([NH2:42])[C:25](=[O:26])[N:24]([CH2:27][C:28]([CH3:31])([CH3:29])[CH3:30])[C:23]3[CH:32]=[CH:33][CH:34]=[CH:35][C:22]=3[N:21]([CH2:36][C:37]([CH3:40])([CH3:39])[CH3:38])[C:20]2=[O:41])=[O:18])[CH3:16])=[O:12])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 1454243,5-Difluorophenylacetic acidHCID 69034686HCID 69034686, compound

Product 1

HCID 86584979HCID 86584979, compound

Procedure

Following General Procedure I above using 3,5-difluorophenylacetic acid (Lancaster) and 3-(L-alaninyl)-amino-2,4dioxo-1,5-bis-(2,2dimethylpropyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine hydrochloride (Example 8-V), the title compound was prepared as a white solid (melting point=194-195° C.). Purification was by flash chromatography eluting with CH2Cl2/EtOAc (2:1 gradient to 3:2). Rf=0.46 (CH2Cl2/EtOAc, 2:1).

Workup

  1. customPurification
  2. washeluting with CH2Cl2/EtOAc (2:1 gradient to 3:2)

Sources & evidence

ORD record
ord-5b39ea02d4dd476fa8460d0be6639120
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Reaction notes

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