Tert-butyl 2-[(2-acetamido-1,3-thiazol-5-yl)sulfanyl]acetate → [[2-(Acetylamino)-5-thiazolyl]thio]acetic acid

HRID 1060241Notes

Reaction equation

HRID 1060241 reaction equation
CC([O:5][C:6](=[O:18])[CH2:7][S:8][C:9]1[S:13][C:12]([NH:14][C:15](=[O:17])[CH3:16])=[N:11][CH:10]=1)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[C:15]([NH:14][C:12]1[S:13][C:9]([S:8][CH2:7][C:6]([OH:18])=[O:5])=[CH:10][N:11]=1)(=[O:17])[CH3:16]

Participants

4

Reactant 1

HCID 5329661Tert-butyl 2-[(2-acetamido-1,3-thiazol-5-yl)sulfanyl]acetate

Product 1

HCID 5329677[[2-(Acetylamino)-5-thiazolyl]thio]acetic acidYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [[2-(acetylamino)-5-thiazolyl]thio]acetic acid 1,1-dimethylethyl ester (4.32 g, 15 mmol) in methylene chloride (30 mL) and trifluoroacetic acid (20 mL) was stirred at rt overnight and concentrated in vacuo. To the residue was added ethyl ether (50 mL). The precipitated solid was collected, washed with ethyl ether and dried to afford the desired product (3.38 g, 97%) as a solid, mp 210° C.

Workup

  1. concentrationconcentrated in vacuo
  2. additionTo the residue was added ethyl ether (50 mL)
  3. customThe precipitated solid was collected
  4. washwashed with ethyl ether
  5. customdried

Sources & evidence

ORD record
ord-94fa6caa475a4f15a6789d9d2641146c
Source dataset
uspto-grants-2003_02
Patent number
US06521759B2

Reaction notes

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