Acetic Acid → Methyl 2-(3-hydroxybutan-2-ylamino)thiazole-4-carboxylate

HRID 872658Notes

Reaction equation

HRID 872658 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1.[OH:11][CH:12]([CH3:16])[C:13](=O)[CH3:14].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[OH:11][CH:12]([CH3:16])[CH:13]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:6]=1)[CH3:14]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 179AcetoinHCID 516892Sodium BicarbonateHCID 840099Methyl 2-amino-1,3-thiazole-4-carboxylateHCID 5049666Sodium triacetoxyborohydride2×

Product 1

HCID 87294675Methyl 2-(3-hydroxybutan-2-ylamino)thiazole-4-carboxylateYield 68.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Methyl 2-aminothiazole-4-carboxylate (1.0, 6.32 mmol), 3-hydroxy-2-butanone (1.045 ml, 12.01 mmol) and acetic acid (2.278 g, 37.9 mmol) were dissolved in 1,2-dichloroethane. Sodium triacetoxy borohydride (3.75 g, 17.70 mmol) was added and the reaction mixture was stirred overnight. Sodium triacetoxy borohydride (3.1 g) was added in two portions and the reaction mixture was stirred over two nights. 1M NaHCO3 was added slowly and mixture was extracted twice with DCM. DCM phase was dried and evaporated to afford 68.1% of the title product. m/z [230.3+1].

Workup

  1. stirringthe reaction mixture was stirred over two nights
  2. extractionmixture was extracted twice with DCM
  3. dry with materialDCM phase was dried
  4. customevaporated

Sources & evidence

ORD record
ord-a6bd3f90f4be4c78ba629aeef51036c1
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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