Methanol → HCID 59822356, compound

HRID 1678490Notes

Reaction equation

HRID 1678490 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:35])[NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][N:27]4[CH2:32][CH2:31][S:30](=[O:34])(=[O:33])[CH2:29][CH2:28]4)=[CH:22][CH:21]=3)=[CH:14][CH:13]=2)[C:8]([CH3:11])=[CH:9][CH:10]=1)=O.[BH4-].[Li+].CO>C1COCC1>[O:34]=[S:30]1(=[O:33])[CH2:31][CH2:32][N:27]([CH2:26][C:23]2[CH:24]=[CH:25][C:20]([NH:19][C:18]([C:15]3[CH:14]=[CH:13][C:12]([C:7]4[CH:6]=[C:5]([CH2:3][OH:2])[CH:10]=[CH:9][C:8]=4[CH3:11])=[CH:17][CH:16]=3)=[O:35])=[CH:21][CH:22]=2)[CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 68257806HCID 68257806, compound

Product 1

HCID 59822356HCID 59822356, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4′-[4-(1,1-Dioxo-1lambda*6*-thiomorpholin-4-ylmethyl)-phenylcarbamoyl]-6-methyl-biphenyl-3-carboxylic acid methyl ester (565 mg) in dry THF (6 ml) was treated with a solution of lithium borohydride (2M in THF, 3.5 ml). The mixture was stirred at 20 C for 18 h. and was then treated with methanol (5 ml). The mixture was then evaporated and the residue partitioned between water and ethyl acetate. The dried extracts were evaporated giving the title compound as a colourless crystalline solid (505 mg).

Workup

  1. customThe mixture was then evaporated
  2. customthe residue partitioned between water and ethyl acetate
  3. customThe dried extracts were evaporated

Sources & evidence

ORD record
ord-c206704bf83b446cb4008462dba9da00
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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