Methanol → HCID 15885282, compound

HRID 2288046Notes

Reaction equation

HRID 2288046 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[CH:8][S:9][C:10]=1[S:11][CH2:12][CH2:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])=O)C.[BH4-].[Li+].CO>C1COCC1>[OH:3][CH2:4][C:6]1[N:7]=[CH:8][S:9][C:10]=1[S:11][CH2:12][CH2:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 15885293Ethyl 5-[[2-(phenylsulfonyl)ethyl]thio]-4-thiazolecarboxylate

Product 1

HCID 15885282HCID 15885282, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-ethoxycarbonyl-5-[2-(phenylsulfonyl)ethylthio]thiazole (702 mg, 2 mmol) in 20 ml of THF was added lithium borohydride (2M, 1 ml) and methanol (0.16 ml, 4 mmol) at -30° C. The reaction mixture was allowed slowly warm up to room temperature and stirred overnight. The solvent was removed under reduced pressure and the crude residue was subjected to chromatography by using dichloromethane and methanol as the eluent to give the title compound (400 mg, 65%). 1H NMR (CDCl3) δ 2.55 (s, 1H), 3.00 (t, 2H, J=6), 3.40 (t, 2H, J=6), 4.71 (s, 2H), 7.6 (t, 2H, J=7), 7.68 (t, 1H, J=7), 7.82 (d, 2H, J=7), and 8.80 (s, 1H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-90d708387faa46fdbf208c316bf9a621
Source dataset
uspto-grants-2000_07
Patent number
US06087355

Reaction notes

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