Methanol → HCID 58236944, compound

HRID 1189017Notes

Reaction equation

HRID 1189017 reaction equation
[CH3:1][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][N:27]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]1[S:15][CH:16]([CH2:19][C:20](OCC)=[O:21])[CH2:17][N:18]=1)=[CH:10]2)[CH3:3].O1CCCC1.CO.[BH4-].[Li+]>O>[CH3:3][CH:2]([O:4][C:5]1[CH:6]=[C:7]([O:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([CH3:35])(=[O:34])=[O:33])=[CH:28][N:27]=2)[CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]1[S:15][CH:16]([CH2:19][CH2:20][OH:21])[CH2:17][N:18]=1)=[CH:10]2)[CH3:1]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 58237092HCID 58237092, compound

Product 1

HCID 58236944HCID 58236944, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl {2-[7-(1-methylethoxy)-5-{[5-(methylsulfonyl)pyridin-2-yl]oxy}-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl}acetate (500 mg), tetrahydrofuran (20 mL) and methanol (5 mL) was added lithium borohydride (110 mg) at 0° C. The whole was stirred at room temperature for 2 h. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=1:2 to 9:1, volume ratio) to give a pale yellow amorphous solid. The solid was crystallized from ethyl acetate-diethyl ether to give the title compound (210 mg, 46%) as pale yellow crystals. The crystals were recrystallized from ethyl acetate-diethyl ether to give pale yellow prisms. MS 476 (MH+). mp 172-173° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (ethyl acetate:hexane=1:2 to 9:1, volume ratio)
  7. customto give a pale yellow amorphous solid
  8. customThe solid was crystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-f6fbf197dc1341839629538e68dcec61
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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