Methanol → HCID 15885282, compound

HRID 377389Notes

Reaction equation

HRID 377389 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) δ2.55 (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-d7260c10c77d4ed097a700e3909f6d58
Source dataset
uspto-grants-2000_02
Patent number
US06025352

Reaction notes

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