Trifluoroacetic acid → (S)-2-(5-Formylthiazol-2-ylamino)-3-methylbutanoic acid

HRID 1755442Notes

Reaction equation

HRID 1755442 reaction equation
[CH:1]([C:3]1[S:7][C:6]([NH:8][C@@H:9]([CH:17]([CH3:19])[CH3:18])[C:10]([O:12]C(C)(C)C)=[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][C@@H:9]([CH:17]([CH3:19])[CH3:18])[C:10]([OH:12])=[O:11])=[N:5][CH:4]=1)=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 131733674(S)-tert-Butyl 2-(5-formylthiazol-2-ylamino)-3-methylbutanoate

Product 1

HCID 89858211(S)-2-(5-Formylthiazol-2-ylamino)-3-methylbutanoic acidYield 200.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure described in Example 3, except using the material from Example 19 (2.99 g, 10.51 mmol), CH2Cl2 (200 mL) and TFA (51 mL, 662 mmol), 4.8 g (quantitative yield) of the title compound is obtained as a tan syrup as a bis TFA salt. LC/MS (Condition A): ret. T=2.33 min, (M+H)+ 229.04.

Sources & evidence

ORD record
ord-eddbc34c4eba495ebb8737e9a197f1a7
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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