Acetone → Tert-butyl 6,6-dimethyl-4-oxo-4,6-dihydrofuro[3,4-d]thiazol-2-ylcarbamate

HRID 1028170Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C:9]1[S:10]C=[C:12]([C:14](OC)=[O:15])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:18](NC(C)C)(C)C.C([Li])CCC.[CH3:30][C:31]([CH3:33])=[O:32]>>[CH3:30][C:31]1([CH3:18])[C:33]2[S:10][C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[N:13][C:12]=2[C:14](=[O:15])[O:32]1

Participants

Reactant 4

HCID 180Acetone

HCID 7912Diisopropylamine

HCID 7213137Methyl 2-Boc-aminothiazole-4-carboxylate

HCID 178418339Butyllithium

Product 1

HCID 86618914Tert-butyl 6,6-dimethyl-4-oxo-4,6-dihydrofuro[3,4-d]thiazol-2-ylcarbamate

Procedure

Methyl 2-(tert-butoxycarbonylamino)thiazole-4-carboxylate (purchased from Combi-Blocks), diisopropylamine, butyllithium, and dry acetone (purchased from Acros) were processed as described in Example 3D to obtain the title compound. MS (ESI+) m/z 285 (M+H)+

Sources & evidence

ORD record: ord-f5cbc1753cb04780bdc5976ae0439063
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735434B2

Reaction notes

Loading…