Water → HCID 58418160, compound

HRID 1037980Notes

Reaction equation

HRID 1037980 reaction equation
[CH:1]([C:3]1[S:4][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:6][N:7]=1)=O.[CH3:15][C:16]([S@@:19]([NH2:21])=[O:20])([CH3:18])[CH3:17].C(=O)([O-])[O-].[Cs+].[Cs+].O>C(Cl)Cl>[C:16]([S@@:19](/[N:21]=[CH:1]/[C:3]1[S:4][C:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[CH:6][N:7]=1)=[O:20])([CH3:18])([CH3:17])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 86657340Tert-butyl 2-formyl-1,3-thiazole-5-carboxylate

Product 1

HCID 58418160HCID 58418160, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-formylthiazole-5-carboxylate (15.7 g, 74 mmol) and (S)-2-methylpropane-2-sulfinamide (10.7 g, 88 mmol) in DCM (750 mL) at 0° C. was added cesium carbonate (48.2 g, 148 mmol). The mixture was warmed to rt and stirred for 8 h. To the solution was added water (200 mL). After separation, the aqueous phase was extracted with DCM (3×200 mL). The combined organic phases were dried (Na2SO4), and concentrated. Flash column chromatography (petroleum ether:EtOAc, 100:1 to 10:1) afforded (S,E)-tert-butyl 2-((tert-butylsulfinylimino)methyl)thiazole-5-carboxylate (18.9 g, 81%). 1H NMR (CDCl3, 400 MHz) δ 8.67 (s, 1H), 8.39 (s, 1H), 1.52 (s, 9H), 1.22 (s, 9H).

Workup

  1. customAfter separation
  2. extractionthe aqueous phase was extracted with DCM (3×200 mL)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b8127cebdffc449fa28cbc3f4ea46f2f
Source dataset
uspto-grants-2013_10
Patent number
US08546588B2

Reaction notes

Loading…