Phenyl chloroformate → HCID 58055074, compound

HRID 1685020Notes

Reaction equation

Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8][N:9]([CH3:19])[C:10]([C:12]2[C:13]([CH3:18])=[N:14][O:15][C:16]=2[CH3:17])=[O:11])[N:7]=1.[C:20]1([O:26][C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>N1C=CC=CC=1.CN(C1C=CN=CC=1)C.O1CCCC1>[C:20]1([O:26][C:27](=[O:28])[NH:2][C:3]2[S:4][CH:5]=[C:6]([CH2:8][N:9]([CH3:19])[C:10]([C:12]3[C:13]([CH3:18])=[N:14][O:15][C:16]=3[CH3:17])=[O:11])[N:7]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-((2-aminothiazol-4-yl)methyl)-N,3,5-trimethylisoxazole-4-carboxamide hydrochloride (6.16 g, 20.34 mmol) was dissolved in pyridine (35 mL) and DMAP (150 mg, 5 mol %) was added. The solution was cooled to 0° C. and a solution of phenylchloroformate (2.55 mL, 3.18 g, 20.34 mmol) in tetrahydrofuran (35 mL) was added dropwise. The mixture was stirred overnight at room temperature and the volatiles were evaporated in vacuo. The residue was taken up in water/EtOAc. The organic phase was dried over MgSO4 and the volatiles were evaporated under reduced pressure. The material was crystallized from EtOAc/i-Pr2O to afford (4-{[methyl(3,5-dimethylisoxazole-4-carbonyl)-amino]-methyl}-thiazol-2-yl) carbamic acid phenyl ester (1.80 g) as a tan-colored solid (purity ˜85%). 1H NMR (CDCl3): δ 9.85 (bs, 1H), 7.45 (m, 2H), 7.25 (m, 2H), 7.20 (m, 2H), 6.80 (b, 1H), 4.75 (bs, 1H), 4.45 (bs, 1H), 3.00 (bs, 3H), 2.36 (s, 3H), 2.24 (s, 3H).

Workup

customthe volatiles were evaporated in vacuo
dry with materialThe organic phase was dried over MgSO4
customthe volatiles were evaporated under reduced pressure
customThe material was crystallized from EtOAc/i-Pr2O

Sources & evidence

ORD record: ord-dcc9c6c5bf694d5d9ab3e034a27cee0c
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148380B2

Reaction notes

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