Trifluoroacetic acid → 920289-29-8

HRID 1983812Notes

Reaction equation

HRID 1983812 reaction equation
C([O:5][C:6](=[O:39])[CH2:7][CH2:8][C@H:9]([NH:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:29][CH:28]=1)=[O:26])[C:10](=[O:23])[NH:11][C:12]([CH3:22])([CH3:21])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)(C)(C)C.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[C:30]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:29]=[CH:28][C:27]([C:25]([NH:24][C@H:9]([C:10](=[O:23])[NH:11][C:12]([CH3:22])([CH3:21])[CH2:13][C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)[CH2:8][CH2:7][C:6]([OH:39])=[O:5])=[O:26])=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24865336HCID 24865336, compound

Product 1

HCID 16048422920289-29-8Yield 92.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of Compound 5 (100 g) in toluene (325 ml) were added trifluoroacetic acid (TFA, 313 g) at 5 to 20° C. The resulting solution was stirred at ambient temperature until the reaction was completed (4 to 6 h). TFA was removed by vacuum distillation, the solution diluted with ethyl acetate, washed with aqueous potassium acetate, and crystallization was affected by adding heptane to afford Compound 6 as white solid (82.7 g, yield 92%; Purity—99.8% (HPLC area %); Strength—98.0%; ee—99.0%). NMR data: 1.37, 1.45-s, 6H, CH3; 2.10-m, 2H, CH2; 2.35-2.60-m, 2H, CH2; 2.80-3.10-d, 2H, CH2; 4.80-q, 1H, CH; 6.80-7.80-m, 13H, Ph; 7.90-s, 2H, NH.

Workup

  1. custom(4 to 6 h)
  2. customTFA was removed by vacuum distillation
  3. additionthe solution diluted with ethyl acetate
  4. washwashed with aqueous potassium acetate, and crystallization
  5. additionby adding heptane

Sources & evidence

ORD record
ord-3fd59fc190884ebbb130969395b8f1c9
Source dataset
uspto-grants-2009_06
Patent number
US07541485B2

Reaction notes

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