3,5-Difluoromandelic acid → HCID 22984127, compound

HRID 411397Notes

Reaction equation

HRID 411397 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.N[C@H](C([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)C>>[F:13][C:11]1[CH:10]=[C:4]([CH:5]([OH:9])[C:6]([NH:43][C@H:20]([C:26]([NH:43][CH:20]2[C:21](=[O:42])[N:22]([CH2:37][C:38]([CH3:41])([CH3:40])[CH3:39])[C:23]3[CH:36]=[CH:35][CH:34]=[CH:33][C:24]=3[N:25]([CH2:28][C:29]([CH3:31])([CH3:30])[CH3:32])[C:26]2=[O:27])=[O:27])[CH3:21])=[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 22984127HCID 22984127, 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-ae42dc4bb38c4dd490b1447205a277dc
Source dataset
uspto-grants-2003_05
Patent number
US06559141B2

Reaction notes

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