Sodium Methoxide → HCID 22726852, compound

HRID 2085967Notes

Reaction equation

HRID 2085967 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([CH2:7][S:8][CH2:9][CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:6]=1.[CH3:19][O-:20].[Na+]>CN(C)C=O>[C:15]([O:14][C:12]([NH:11][CH2:10][CH2:9][S:8][CH2:7][C:5]1[N:6]=[C:2]([O:20][CH3:19])[S:3][CH:4]=1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 22726892HCID 22726892, compound

Product 1

HCID 22726852HCID 22726852, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 2-bromo-4-[(2-tert-butoxycarbonylaminoethyl)thiomethyl]-1,3-thiazole (650 mg, 1.85 mmol) in N,N-dimethylformamide (5 mL) was added sodium methoxide (300 mg, 5.56 mmol) and stirred at 45° C. for 3 days. The reaction was quenched with water and the mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with aqueous lithium chloride and concentrated. The residue was chromatographed on silica gel (10% ethyl acetate-hexane), affording 184 mg of the title compound. 1H NMR (CDCl3) δ 1.54 (9H), 2.78 (t, 2H), 3.42 (m, 2H), 3.74 (s, 2H), 4.18 (s, 3H), 5.24 (br s, 1H), 6.60 (s, 1H).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with aqueous lithium chloride
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (10% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-d951fe572e3a4c4b89361a0cea3eb1f4
Source dataset
uspto-grants-2004_04
Patent number
US06723716B1

Reaction notes

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