Bromopyruvic Acid → 2-(1-(Tert-butyldiphenylsilyloxy)ethyl)thiazole-4-carboxylic acid

HRID 872859Notes

Reaction equation

HRID 872859 reaction equation
Br[CH2:2][C:3](=O)[C:4]([OH:6])=[O:5].[Si:8]([O:25][CH:26]([CH3:30])[C:27](=[S:29])[NH2:28])([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1>[Si:8]([O:25][CH:26]([C:27]1[S:29][CH:2]=[C:3]([C:4]([OH:6])=[O:5])[N:28]=1)[CH3:30])([C:21]([CH3:22])([CH3:23])[CH3:24])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 70684Bromopyruvic AcidHCID 872949642-(Tert-butyldiphenylsilyloxy)propanethioamide

Product 1

HCID 671683752-(1-(Tert-butyldiphenylsilyloxy)ethyl)thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A flask containing 3-bromopyruvic acid (317 mg, 1.901 mmol) was put under nitrogen atmosphere. 2-(tert-butyldiphenylsilyloxy)propanethioamide (653 mg, 1.901 mmol) was dissolved in dry THF (8 ml) and added through a septum. The following mixture was refluxed for two hours and then allowed to cool to RT. The solvent was evaporated and extracted with DCM/water and the combined organic phases were evaporated. 1H-NMR (400 MHz; DMSO-d6): δ 1.07 (s, 9H), 1.35 (d, 3H), 5.14 (q, 1H), 7.39-7.54 (m, 2H), 7.57-7.61 (m, 2H), 7.26-7.69 (m, 2H), 8.38 (s, 1H).

Workup

  1. additionadded through a septum
  2. temperatureThe following mixture was refluxed for two hours
  3. customThe solvent was evaporated
  4. extractionextracted with DCM/water
  5. customthe combined organic phases were evaporated

Sources & evidence

ORD record
ord-91ea92c1b04148778cc3f1751a3ff820
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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