Hydrochloric Acid → HCID 57437184, compound

HRID 2064741Notes

Reaction equation

HRID 2064741 reaction equation
[CH2:1](OC(OCC)CBr)[CH3:2].Cl.C([O-])(O)=O.[Na+].[CH3:16][O:17][C:18]([C:20]1[S:24][C:23]([NH2:25])=[N:22][C:21]=1[CH3:26])=[O:19]>O.O1CCOCC1>[CH3:16][O:17][C:18]([C:20]1[S:24][C:23]2=[N:25][CH:1]=[CH:2][N:22]2[C:21]=1[CH3:26])=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 516892Sodium BicarbonateHCID 713653methyl 2-amino-4-methylthiazole-5-carboxylate

Product 1

HCID 57437184HCID 57437184, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of bromoacetaldehyde diethyl acetal (29.3 mmol, 1.26 eq) in water (200 mL) is treated dropwise with conc. hydrochloric acid (3.0 mL), stirred for 14 h at RT and heated for additional 30 min at 80° C. After cooling to RT NaHCO3 (37.9 mmol) is added carefully and the mixture is stirred for 2 h and treated with 2-Amino-4-methyl-thiazole-5-carboxylic acid methyl ester (23.2 mmol, 1.00 eq). After 1 h dioxane (130 mL) is added and the mixture is stirred at RT for 30 min and at 100° C. for 48 h. The organic solvents are removed in vacuo and the mixture is extracted several times with DCM and chloroform. The combined organic layers are dried over Na2SO4 and concentrated in vacuo to give the desired ester which is used without further purification. LC-MS: tR=0.55 min; [M+H]+=197.0.

Workup

  1. temperatureheated for additional 30 min at 80° C
  2. additionis added carefully
  3. stirringthe mixture is stirred for 2 h
  4. stirringthe mixture is stirred at RT for 30 min and at 100° C. for 48 h
  5. customThe organic solvents are removed in vacuo
  6. extractionthe mixture is extracted several times with DCM and chloroform
  7. dry with materialThe combined organic layers are dried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-801de152612d4cc2b433a47808d72f5b
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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