Tetrahydrofuran → HCID 59331231, compound

HRID 1882059Notes

Reaction equation

HRID 1882059 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[S:27][C:28](/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:29][N:30]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.O1CCCC1>[C].[Pd].C(O)C>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[S:27][C:28]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:29][N:30]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:5])=[O:6])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 59331250HCID 59331250, compound

Product 1

HCID 59331231HCID 59331231, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl (2E)-3-[2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-1,3-thiazol-5-yl]propenoate (0.78 g), 10% palladium carbon (containing 50% water, 0.15 g), tetrahydrofuran (10 mL) and ethanol (5 mL) was stirred under hydrogen atmosphere at room temperature for 2 days. The insoluble material was filtered off, and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography, and the title compound (0.58 g, yield 79%) was obtained as a yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). MS: 543 (MH+).

Workup

  1. filtrationThe insoluble material was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-918a7a2053b9498faf013890723c97c1
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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