Water → HCID 68992203, compound

HRID 661073Notes

Reaction equation

HRID 661073 reaction equation
Cl([O-])=O.[Na+].[Br:5][C:6]1[N:7]=[C:8](NC(=O)OC(C)(C)C)[S:9][C:10]=1[CH:11]=[O:12].[CH2:21]([OH:25])C(C)C.P([O-])(O)(O)=[O:27].[Na+].[CH3:32][C:33](=[CH:35]C)[CH3:34].[OH2:37]>>[Br:5][C:6]1[N:7]=[C:8]([C:21]([O:25][C:33]([CH3:35])([CH3:34])[CH3:32])=[O:27])[S:9][C:10]=1[C:11]([OH:12])=[O:37]

Participants

7

Reactant 6

HCID 962WaterHCID 6560IsobutanolHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 45117881HCID 45117881, compound

Product 1

HCID 68992203HCID 68992203, compoundYield 109%

Procedure

To a 250 mL round-bottomed flask was added sodium chlorite (3.68 g, 40.7 mmol), tert-butyl 4-bromo-5-formylthiazol-2-ylcarbamate (1.18 g, 3.84 mmol), isobutanol (76.8 mL, 3.84 mmol), and an aqueous (30.00 mL, 3.84 mmol) solution of sodium dihydrogen phosphate (3.60 g, 30.0 mmol) followed by 2-methyl-2-butene (4.47 mL, 42.3 mmol). The mixture was stirred vigorously for about 3 hours. LCMS indicated complete conversion to product so the mixture was diluted with water (60 mL) and 120 mL of 1:1 EtOAc/hexanes. The aqueous layer was extracted with 1:1 EtOAc/hexanes, and the combined organic layers were washed with brine, dried over sodium sulfate, and filtered. The solvent was reduced providing the semi-crude product 4-bromo-2-(tert-butoxycarbonyl)thiazole-5-carboxylic acid (1.35 g, 109% yield). The crude product was used immediately without further purification.

Workup

  1. extractionThe aqueous layer was extracted with 1:1 EtOAc/hexanes
  2. washthe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-9ff4e19c900c495ea97b5a27f081ae38
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

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