3,5-Difluorophenylacetic acid → HCID 69271053, compound

HRID 133290Notes

Reaction equation

HRID 133290 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([NH2:40])[C:25](=[O:26])[N:24]([CH2:27][CH:28]2[CH2:30][CH2:29]2)[C:23]2[CH:31]=[CH:32][CH:33]=[CH:34][C:22]=2[N:21]([CH2:35][CH:36]2[CH2:38][CH2:37]2)[C:20]1=[O:39])=[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([NH2:40])[C:25](=[O:26])[N:24]([CH2:27][CH:28]3[CH2:29][CH2:30]3)[C:23]3[CH:31]=[CH:32][CH:33]=[CH:34][C:22]=3[N:21]([CH2:35][CH:36]3[CH2:38][CH2:37]3)[C:20]2=[O:39])=[O:18])[CH3:16])=[O:12])[CH:3]=[C:2]([F:1])[CH:7]=1

Participants

3

Reactant 2

HCID 1454243,5-Difluorophenylacetic acidHCID 69033314HCID 69033314, 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-0858a2f23d05436a81443a29f798e04b
Source dataset
uspto-grants-2008_06
Patent number
US07390801B2

Reaction notes

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