Acetic Acid → HCID 4737550, compound

HRID 2219669Notes

Reaction equation

HRID 2219669 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([CH3:14])[N:13]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH:1]1([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 7967Cyclohexanone2×HCID 741432-Amino-4-methylthiazoleHCID 5049666Sodium triacetoxyborohydride2×

Product 1

HCID 4737550HCID 4737550, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.85 mL (8.28 mmol) of cyclohexanone and 1.0 g (8.75 mmol) of 2-amino-4-methylthiazole in 10 mL of tetrahydrofuran was added 0.5 mL (8.75 mmol) of acetic acid and 4.64 g (21.8 mmol) of sodium triacetoxyborohydride. After stirring for 16 hr at rt, a further 0.45 mL (4.37 mmol) of cyclohexanone and 0.926 g (4.37 mmol) of sodium triacetoxyborohydride was added and stirring continued for 72 hr at rt. Ethyl acetate (15 mL) was added and the mixture washed with saturated sodium bicarbonate (2×15 mL) then dried (Na2SO4). Purification by chromatography on silica gave the title compound.

Workup

  1. stirringstirring
  2. waitcontinued for 72 hr at rt
  3. washthe mixture washed with saturated sodium bicarbonate (2×15 mL)
  4. dry with materialthen dried (Na2SO4)
  5. customPurification by chromatography on silica

Sources & evidence

ORD record
ord-cecbfd673d4743fc884947d7dc8bbb33
Source dataset
uspto-grants-2008_08
Patent number
US07414067B2

Reaction notes

Loading…