3,5-Difluorophenylacetic acid → HCID 69271053, compound

HRID 411393Notes

Reaction equation

HRID 411393 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]([CH2:28][CH:29]2[CH2:31][CH2:30]2)[C:24]2[CH:32]=[CH:33][CH:34]=[CH:35][C:23]=2[N:22]([CH2:36][CH:37]2[CH2:39][CH2:38]2)[C:21]1=[O:40])=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:26](=[O:27])[N:25]([CH2:28][CH:29]3[CH2:31][CH2:30]3)[C:24]3[CH:32]=[CH:33][CH:34]=[CH:35][C:23]=3[N:22]([CH2:36][CH:37]3[CH2:39][CH2:38]3)[C:21]2=[O:40])=[O:27])[CH3:21])=[O:12])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 1454243,5-Difluorophenylacetic acidHCID 23552768HCID 23552768, compound

Product 1

HCID 69271053HCID 69271053, compound

Procedure

Following General Procedure I above using 3,5-difluorophenylacetic acid (Lancaster) and 3-(L-alaninyl)-amino-2,4-dioxo-1,5-bis-(cyclopropylmethyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine hydrochloride (Example 8-U), the title compound was prepared as a white solid (melting point=211-212° C.). Purification was by flash chromatography eluting with CH2Cl2/EtOAc (1:1 gradient to 2:3). Rf=0.44 (CH2Cl2/EtOAc, 1:1).

Workup

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

Sources & evidence

ORD record
ord-303ffbde534647b58b98621a839a0d9a
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Reaction notes

Loading…