Sodium borohydride → N-{[4'-({[4-(1-hydroxyethyl)-3-methyl-1-benzofuran-2-yl]carbonyl}amino)-1,1'-biphenyl-4-yl]sulfonyl}-L-valine

HRID 29332Notes

Reaction equation

HRID 29332 reaction equation
[C:1]([C:4]1[C:9]2[C:10]([CH3:39])=[C:11]([C:13]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][C:25]([S:28]([NH:31][C@H:32]([C:36]([OH:38])=[O:37])[CH:33]([CH3:35])[CH3:34])(=[O:30])=[O:29])=[CH:24][CH:23]=4)=[CH:18][CH:17]=3)=[O:14])[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(C1C2C(C)=C(C(NC3C=CC(C4C=CC(S(N[C@H](C(OC)=O)C(C)C)(=O)=O)=CC=4)=CC=3)=O)OC=2C=CC=1)(=O)C.[BH4-].[Na+]>C(O)C>[OH:3][CH:1]([C:4]1[C:9]2[C:10]([CH3:39])=[C:11]([C:13]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([C:22]4[CH:27]=[CH:26][C:25]([S:28]([NH:31][C@H:32]([C:36]([OH:38])=[O:37])[CH:33]([CH3:34])[CH3:35])(=[O:29])=[O:30])=[CH:24][CH:23]=4)=[CH:20][CH:21]=3)=[O:14])[O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 11330264N-[(4'-{[(4-acetyl-3-methyl-1-benzofuran-2-yl)carbonyl]amino}-1,1'-biphenyl-4-yl)sulfonyl]-L-valineHCID 68713373methyl N-[(4'-{[(4-acetyl-3-methyl-1-benzofuran-2-yl)carbonyl]amino}-1,1'-biphenyl-4-yl)sulfonyl]-L-valinate

Product 1

HCID 59788425N-{[4'-({[4-(1-hydroxyethyl)-3-methyl-1-benzofuran-2-yl]carbonyl}amino)-1,1'-biphenyl-4-yl]sulfonyl}-L-valineYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.05 g of N-[(4′-{[(4-acetyl-3-methyl-1-benzofuran-2-yl)carbonyl]amino}-1,1′-biphenyl-4-yl)sulfonyl]-L-valine, the product of Example 94, Step 3, in 18 mL of ethanol was added 0.01 g of sodium borohydride and the reaction was stirred at room temperature for 2 hours. The reaction was quenched with 1N HCl, adjusting to ˜pH3. The reaction mixture was concentrated in vacuo and the residue was then extracted with ethyl acetate. The organic layer was washed with water, brine, dried over Na2SO4, filtered, and concentrated to provide 0.037 g of N-{[4′-({[4-(1-hydroxyethyl)-3-methyl-1-benzofuran-2-yl]carbonyl}amino)-1,1′-biphenyl-4-yl]sulfonyl}-L-valine. Yield 74%. m.p. 148° C.(d); MS: 549.1(M−H)−.

Workup

  1. customThe reaction was quenched with 1N HCl
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionthe residue was then extracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-97a1cdc7fe414f2288ca5ed81a450565
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

Loading…