Trifluoroacetic acid → (2S)-2-((2S)-2-(2-(5-Formylthiazol-2-ylamino)-3-methylbutanamido)propanamido)propanoic acid

HRID 1755447Notes

Reaction equation

HRID 1755447 reaction equation
[CH:1]([C:3]1[S:7][C:6]([NH:8][CH:9]([CH:27]([CH3:29])[CH3:28])[C:10]([NH:12][C@@H:13]([CH3:26])[C:14]([NH:16][C@@H:17]([CH3:25])[C:18]([O:20]C(C)(C)C)=[O:19])=[O:15])=[O:11])=[N:5][CH:4]=1)=[O:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]([C:3]1[S:7][C:6]([NH:8][CH:9]([CH:27]([CH3:29])[CH3:28])[C:10]([NH:12][C@@H:13]([CH3:26])[C:14]([NH:16][C@@H:17]([CH3:25])[C:18]([OH:20])=[O:19])=[O:15])=[O:11])=[N:5][CH:4]=1)=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 89867008(2S)-tert-Butyl 2-((2S)-2-(2-(5-formylthiazol-2-ylamino)-3-methylbutanamido)propanamido)propanoate

Product 1

HCID 89858110(2S)-2-((2S)-2-(2-(5-Formylthiazol-2-ylamino)-3-methylbutanamido)propanamido)propanoic acidYield 145.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure as described in Example 11, except using material from Example 26 (213 mg, 0.499 mmol), CH2Cl2 (75 mL) and TFA (25 mL, 324 mmol), 268.4 mg (quantitative yield) of the title compound is obtained as a white solid as a mono TFA salt. LC/MS (Condition A): ret. T=2.15 min, (M+H)+ 371.14.

Sources & evidence

ORD record
ord-82daa52006804221a035e4477c7d8b38
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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