Trifluoroacetic acid → HCID 86604041, compound

HRID 2222951Notes

Reaction equation

HRID 2222951 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:41])[C@@H:12]([NH:20][C:21](=[O:40])[CH:22]([NH:32]C(OC(C)(C)C)=O)[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([F:31])[CH:24]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:8][CH:9]=1)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:41])[C@@H:12]([NH:20][C:21](=[O:40])[CH:22]([NH2:32])[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([F:31])[CH:24]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:8][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86760669HCID 86760669, compound

Product 1

HCID 86604041HCID 86604041, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

2-{(S)-2-[2-tert-Butoxycarbonylamino-2-(3-fluoro-4-methoxy-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester (0.98 g, 2.28 mmol) was taken into dry dichloromethane (20 mL) under argon and cooled in an ice bath. To this was added trifluoroacetic acid (10 mL, 130 mmol) and the mixture was stirred at 0° C. for 1 hour. The reaction mixture was then concentrated to dryness. The oil was dissolved in dichloromethane and precipited with ether and the resulting suspension stirred for 15 minutes. The precipitate was isolated by filtration, washed with ether and dried to give a tan solid. The solid was dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate. The organic solution was dried over sodium sulfate, filtered, concentrated and dried to give 2-{(S)-2-[2-amino-2-(3-fluoro-4-methoxy-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester as a tan foam (0.70 g, 92%).

Workup

  1. temperaturecooled in an ice bath
  2. concentrationThe reaction mixture was then concentrated to dryness
  3. dissolutionThe oil was dissolved in dichloromethane
  4. stirringthe resulting suspension stirred for 15 minutes
  5. customThe precipitate was isolated by filtration
  6. washwashed with ether
  7. customdried
  8. customto give a tan solid
  9. washwashed with saturated aqueous sodium bicarbonate
  10. dry with materialThe organic solution was dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customdried

Sources & evidence

ORD record
ord-57e6ecab0d15437fbfad855876549216
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

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