3,5-Difluoromandelic acid → HCID 131723831, compound

HRID 1841071Notes

Reaction equation

HRID 1841071 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([F:13])[CH:12]=1)[CH:5]([OH:9])[C:6]([OH:8])=O.Cl.[NH2:15][C@H:16]([C:18]([C:20]1([NH2:43])[C:26](=[O:27])[N:25]([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:24]2[CH:33]=[CH:34][CH:35]=[CH:36][C:23]=2[N:22]([CH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])[C:21]1=[O:42])=[O:19])[CH3:17]>>[F:13][C:11]1[CH:10]=[C:4]([CH:5]([OH:9])[C:6]([NH:15][C@H:16]([C:18]([C:20]2([NH2:43])[C:26](=[O:27])[N:25]([CH2:28][C:29]([CH3:32])([CH3:30])[CH3:31])[C:24]3[CH:33]=[CH:34][CH:35]=[CH:36][C:23]=3[N:22]([CH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])[C:21]2=[O:42])=[O:19])[CH3:17])=[O:8])[CH:3]=[C:2]([F:1])[CH:12]=1

Participants

3

Reactant 2

HCID 5886483,5-Difluoromandelic acidHCID 69034686HCID 69034686, compound

Product 1

HCID 131723831HCID 131723831, compound

Procedure

Following General Procedure I above using 3,5-difluoromandelic acid (Lancaster) and 3-(L-alaninyl)-amino-2,4-dioxo-1,5-bis-(2,2-dimethylpropyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine hydrochloride (Example 8-V), the title compound was prepared as a white solid (melting point=116-126° C.). Purification was by flash chromatography eluting with CH2Cl2/EtOAc (1:1 gradient to 2:3). Rf=0.54 and 0.40 (CH2Cl2/EtOAc, 1:1).

Workup

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

Sources & evidence

ORD record
ord-f2661e54d54b44f0ac692c47f4b62205
Source dataset
uspto-grants-2004_01
Patent number
US06683075B1

Reaction notes

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