Trifluoroacetic acid → HCID 59875738, compound

HRID 1700976Notes

Reaction equation

HRID 1700976 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]([CH3:52])([CH3:51])[C@H:10]([NH:22][C:23]([C@H:25]([CH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[C:39]([F:50])[CH:38]=1)[CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])=[O:24])[C:11]([NH:13][C@@H:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15])=[O:12]>ClCCl>[CH3:51][C:9]([CH3:8])([CH3:52])[C@H:10]([NH:22][C:23]([C@H:25]([CH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[C:39]([F:50])[CH:38]=1)[CH2:26][C:27]([OH:29])=[O:28])=[O:24])[C:11]([NH:13][C@@H:14]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57249315HCID 57249315, compound

Product 1

HCID 59875738HCID 59875738, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added dropwise over 5 min to a stirred solution of tert-butyl (3R)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3-fluoro-4-phenoxyphenyl)hexanoate (876 mg, 1.41 mmol) in anhydrous dichloromethane (6 mL) under nitrogen at 20° C. The solution was stirred for 16 h and concentrated under reduced pressure. The residue was dissolved in toluene and concentrated under reduced pressure (twice). Purification by flash chromatography (eluting with hexane:ethyl acetate:acetic acid=75:25:1) gave the title compound as a yellow gum (784 mg, 98%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in toluene
  3. concentrationconcentrated under reduced pressure (twice)
  4. customPurification
  5. washby flash chromatography (eluting with hexane:ethyl acetate:acetic acid=75:25:1)

Sources & evidence

ORD record
ord-6bbfb9010ed143ff83bedfe7b79c75a3
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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