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

HRID 1637234Notes

Reaction equation

HRID 1637234 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. 1H NMR (CD3OD) δ7.48 (s, 1 H), 3.47 (s, 2 H), 2.20 (s, 3 H) ppm; MS m/e 231 (M-H)- ; HPLC (Column: Zorbax Rapid resolution C-18; flow rate: 2.5 mL/min; solvent system: 0-100% B in 8 min. Solvent A: 10% MeOH-90% water-0.2%H3PO4 ; Solvent B: 90% MeOH-10% Water-0.2% H3PO4 ; UV: 254 nm): retention time 4.32 min.

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-92cccbe12346445f800e1d0737347d78
Source dataset
uspto-grants-2000_03
Patent number
US06040321

Reaction notes

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