Calcium Carbonate → 2-(tert-Butoxycarbonylaminomethyl)-4-methylthiazole-5-carboxylic acid ethyl ester

HRID 1376616Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][C:10](=[S:12])[NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH:14]([C:20]([CH3:22])=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[Ca+2]>C(O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[S:12][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:20]([CH3:22])[N:11]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 5.02 g of (tert-butoxycarbonylamino)acetothioamide in 75 ml of ethanol were added 3.92 ml of ethyl 2-chloroacetoacetate and 2.75 g of calcium carbonate, and the mixture was stirred at 50° C. for 6 hours. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluting with a 5:1 mixture of toluene and ethyl acetate to give 5.65 g (yield 71%) of the title compound.

Workup

filtrationThe reaction solution was filtered
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography
washeluting with a 5:1 mixture of toluene and ethyl acetate

Sources & evidence

ORD record: ord-2abacfe40f3c4aa187382bbd926eb771
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05663162

Reaction notes

Loading…