Hydrochloric Acid → 2-[3-(Tert-butoxycarbonyl-methyl-amino)-prop-1-ynyl]-thiazole-4-carboxylic acid

HRID 470719Notes

Reaction equation

HRID 470719 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([C:11]#[C:12][CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:15])[S:9][CH:10]=1)=[O:5])C.[OH-].[Na+].Cl>C1COCC1>[C:19]([O:18][C:16]([N:14]([CH3:15])[CH2:13][C:12]#[C:11][C:8]1[S:9][CH:10]=[C:6]([C:4]([OH:5])=[O:3])[N:7]=1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 672525092-[3-(Tert-butoxycarbonyl-methyl-amino)-prop-1-ynyl]-thiazole-4-carboxylic acid ethyl ester

Product 1

HCID 672524842-[3-(Tert-butoxycarbonyl-methyl-amino)-prop-1-ynyl]-thiazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[3-(tert-butoxycarbonyl-methyl-amino)-prop-1-ynyl]-thiazole-4-carboxylic acid ethyl ester (1.22 g, 3.76 mmol) in THF (10 mL) was added aqueous solution of sodium hydroxide (2 M, 2.82 mL, 5.64 mmol) at RT. After stirring 3 h at RT, the reaction mixture was acidified with 2M aqueous solution of HCl until pH 2, and the solution was extracted with ethylacetate (20 mL). The aqueous layer was re-extracted with ethylacetate (20 mL) and the combined organic layers were washed with brine (10 mL), dried over sodium sulfate, filtered, and evaporated under reduced pressure to 2-[3-(tert-butoxycarbonyl-methyl-amino)-prop-1-ynyl]thiazole-4-carboxylic acid (1.11 g, quant.), which can be used in the next step without further purification. 1H-NMR (400 MHz, d6-DMSO): δ=13.2 (br, 1H), 8.55 (s, 1H), 4.37 (s, 2H), 2.89 (s, 3H), 1.45 (s, 9H). MS: m/z=297 (M+1).

Workup

  1. extractionthe solution was extracted with ethylacetate (20 mL)
  2. extractionThe aqueous layer was re-extracted with ethylacetate (20 mL)
  3. washthe combined organic layers were washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure to 2-[3-(tert-butoxycarbonyl-methyl-amino)-prop-1-ynyl]thiazole-4-carboxylic acid (1.11 g, quant.), which
  7. customcan be used in the next step without further purification

Sources & evidence

ORD record
ord-bf2cd5468fac465eb1ee21931ad601e5
Source dataset
uspto-grants-2014_01
Patent number
US08629286B2

Reaction notes

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