Cornforth reagent → HCID 69285463, compound

HRID 2225294Notes

Reaction equation

HRID 2225294 reaction equation
[OH:1][C@H:2]([C@H:6]1[CH2:11][C@H:10]([N:12]([CH:14]([CH3:16])[CH3:15])[CH3:13])[CH2:9][CH2:8][C@H:7]1[NH:17][C:18](=[O:33])[CH2:19][NH:20][C:21](=[O:32])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1)[CH:3]([CH3:5])[CH3:4].C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[C:2]([C@H:6]1[CH2:11][C@H:10]([N:12]([CH:14]([CH3:16])[CH3:15])[CH3:13])[CH2:9][CH2:8][C@H:7]1[NH:17][C:18](=[O:33])[CH2:19][NH:20][C:21](=[O:32])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1)(=[O:1])[CH:3]([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 69284578HCID 69284578, compound

Product 1

HCID 69285463HCID 69285463, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2-((1R,2S,4R)-2-((S)-1-hydroxy-2-methylpropyl)-4-(isopropyl(methyl)amino)cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide (250 mg, 0.53 mmol; See Example 81, Step 6) in CH2Cl2 (15 mL) was added PDC (599 mg, 1.5 mmol), and 4A molecular sieves (excess). The reaction was stirred for 16 h at RT and then filtered, and concentrated in vacuo. The residue was purified by HPLC to N-(2-((1R,2S,4R)-2-isobutyryl-4-(isopropyl(methyl)amino)cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide. MS found: (M+H)+=470.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by HPLC to N-(2-((1R,2S,4R)-2-isobutyryl-4-(isopropyl(methyl)amino)cyclohexylamino)-2-oxoethyl)-3-(trifluoromethyl)benzamide

Sources & evidence

ORD record
ord-157c6eabab6a4e2ab6d57ab421c869e6
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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