تفاعل #959840

ord-a6bd3f90f4be4c78ba629aeef51036c1

معادلة التفاعل

CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
Sodium triacetoxy borohydride
O=C([O-])O.[Na+]
NaHCO3
COC(=O)c1csc(N)n1
Methyl 2-aminothiazole-4-carboxylate
CC(=O)C(C)O
3-hydroxy-2-butanone
CC(=O)O
acetic acid
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
Sodium triacetoxy borohydride
COC(=O)c1csc(NC(C)C(C)O)n1
title product
المردود 68.1%
COC(=O)c1csc(NC(C)C(C)O)n1
Methyl 2-(3-hydroxybutan-2-ylamino)thiazole-4-carboxylate
المردود 68.1%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.STIRRINGthe reaction mixture was stirred over two nights
  2. 2
    استخلاصmixture was extracted twice with DCM
  3. 3
    تجفيفDCM phase was dried
  4. 4
    أخرىevaporated

الإجراء التجريبي

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].

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08975254B2uspto-grants-2015_03