Acetic Anhydride → Tert-butyl ((4-cyanothiazol-2-YL)methyl)carbamate

HRID 983387Notes

Reaction equation

HRID 983387 reaction equation
[C:1]([NH:8][CH2:9][C:10]1[S:11][CH:12]=[C:13]([C:15]([NH2:17])=O)[N:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.C(OC(=O)C)(=O)C>ClCCl>[C:1]([NH:8][CH2:9][C:10]1[S:11][CH:12]=[C:13]([C:15]#[N:17])[N:14]=1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 108689442-(N-Boc-aminomethyl)thiazole-4-carboxamide

Product 1

HCID 22560011Tert-butyl ((4-cyanothiazol-2-YL)methyl)carbamateYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of 2-(N-Boc-aminomethyl)thiazole-4-carboxamide (200 mg, 0.78 mmol, see Angew. Chem. Int. Ed. Engl. 1996, 35, 1503) in dichloromethane (7 mL) was added triethylamine (0.32 mL, 2.34 mmol) and acetic anhydride (0.22 mL, 1.56 mmol) and the mixture stirred for 1 h. After the solvent was removed, the residue was purified by column chromatography (EtOAc: n-hexane, 3:7). 2-(N-Boc-aminomethyl)thiazole-4-carbonitrile (150 mg, 0.627 mmol) thus obtained was dissolved in methanol (10 mL) and cooled to 0° C. To this was added dropwise acetylchloride (30 equivalent) and the mixture stirred for 1 h at rt. The solvent was removed in vacuo to give the title compound (90 mg, 81%).

Workup

  1. customAfter the solvent was removed
  2. customthe residue was purified by column chromatography (EtOAc: n-hexane, 3:7)

Sources & evidence

ORD record
ord-925f657649d84a96b1e976557fb181c5
Source dataset
uspto-grants-2005_03
Patent number
US06864249B2

Reaction notes

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