2-Methyl-2-butene → 2-(1-{[(Tert-butoxy)carbonyl]amino}ethyl)-1,3-thiazole-5-carboxylic acid

HRID 588500Notes

Reaction equation

HRID 588500 reaction equation
[CH:1]([C:3]1[S:7][C:6]([CH:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[N:5][CH:4]=1)=[O:2].O.O.P([O-])(O)(O)=[O:21].[Na+].CC(=CC)C.Cl([O-])=O.[Na+]>C(O)(C)(C)C.O>[C:13]([O:12][C:11]([NH:10][CH:8]([C:6]1[S:7][C:3]([C:1]([OH:21])=[O:2])=[CH:4][N:5]=1)[CH3:9])=[O:17])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 86657335Tert-butyl 1-(5-formylthiazol-2-yl)ethylcarbamate

Product 1

HCID 673960092-(1-{[(Tert-butoxy)carbonyl]amino}ethyl)-1,3-thiazole-5-carboxylic acidYield 61.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A mixture of tert-butyl 1-(5-formylthiazol-2-yl)ethylcarbamate (3.5 g, 0.014 mol), sodium dihydrogen phosphate dihydrate (2.9 g, 0.019 mol) and 2-methyl-2-butene (3.85 g, 0.055 mol) in tert-butyl alcohol (70 ml) and water (40 mL) was stirred at room temperature for 30 minutes. Sodium chlorite (3.22 g, 0.035 mol) was added and the reaction maintained at room temperature for an additional 2 hours. The reaction was concentrated, diluted with water (50 mL) and acidified (pH=4) with the addition of 3N H3PO4. The mixture was extracted with DCM, the organic layer dried over anhydrous Na2SO4 and evaporated to dryness to afford 2-(1-(tert-butoxycarbonylamino)ethyl)thiazole-5-carboxylic acid (2.35 g, 60%). LC-MS: (FA) ES+ 273.

Workup

  1. temperaturethe reaction maintained at room temperature for an additional 2 hours
  2. concentrationThe reaction was concentrated
  3. additiondiluted with water (50 mL)
  4. additionwith the addition of 3N H3PO4
  5. extractionThe mixture was extracted with DCM
  6. dry with materialthe organic layer dried over anhydrous Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-70f31c8f91b149c1b20024a757314c11
Source dataset
uspto-grants-2016_01
Patent number
US09227951B2

Reaction notes

Loading…