Trifluoroacetic acid → (3R)-3-({[(1S)-2,2-Dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3-methyl-4-phenoxyphenyl)hexanoic acid

HRID 1700979Notes

Reaction equation

HRID 1700979 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]([CH3:50])[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]([CH3:50])[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 59875747tert-butyl (3R)-3-({[(1S)-2,2-dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3-methyl-4-phenoxyphenyl)hexanoate

Product 1

HCID 57238483(3R)-3-({[(1S)-2,2-Dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]amino}carbonyl)-6-(3-methyl-4-phenoxyphenyl)hexanoic acidYield 127.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2.5 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-methyl-4-phenoxyphenyl)hexanoate (550 mg, 0.9 mmol) in anhydrous dichloromethane (5 mL) under nitrogen at 20° C. The solution was stirred for 1 h and concentrated under reduced pressure. The residue was diluted with hydrochloric acid (2M) and extracted with three portions of ethyl acetate. The combined organic solutions were washed with saturated aqueous sodium chloride, dried (MgSO4) and concentrated under reduced pressure. Two portions of toluene were added and evaporated to give the title compound as a yellow gum (640 mg), contaminated with toluene and trifluoroacetic acid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with hydrochloric acid (2M)
  3. extractionextracted with three portions of ethyl acetate
  4. washThe combined organic solutions were washed with saturated aqueous sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. additionTwo portions of toluene were added
  8. customevaporated

Sources & evidence

ORD record
ord-203665f429094eda99db637cf707d8af
Source dataset
uspto-grants-2002_02
Patent number
US06350907B1

Reaction notes

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