Tetrahydrofuran → methyl N-[(4'-{[(5-ethyl-4-hydroxy-3-methyl-1-benzofuran-2-yl)carbonyl]amino}-1,1'-biphenyl-4-yl)sulfonyl)-L-valinate

HRID 29325Notes

Reaction equation

HRID 29325 reaction equation
C([O:8][C:9]1[C:14]2[C:15]([CH3:45])=[C:16]([C:18]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH:32]=[CH:31][C:30]([S:33]([NH:36][C@H:37]([C:41]([O:43][CH3:44])=[O:42])[CH:38]([CH3:40])[CH3:39])(=[O:35])=[O:34])=[CH:29][CH:28]=4)=[CH:23][CH:22]=3)=[O:19])[O:17][C:13]=2[CH:12]=[CH:11][C:10]=1[CH2:46][CH3:47])C1C=CC=CC=1.C1COCC1>CO.[Pd]>[CH2:46]([C:10]1[CH:11]=[CH:12][C:13]2[O:17][C:16]([C:18]([NH:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]4[CH:28]=[CH:29][C:30]([S:33]([NH:36][C@H:37]([C:41]([O:43][CH3:44])=[O:42])[CH:38]([CH3:40])[CH3:39])(=[O:34])=[O:35])=[CH:31][CH:32]=4)=[CH:25][CH:26]=3)=[O:19])=[C:15]([CH3:45])[C:14]=2[C:9]=1[OH:8])[CH3:47]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 68710042methyl N-{[4'-({[4-(benzyloxy)-5-ethyl-3-methyl-1-benzofuran-2-yl]carbonyl}amino)-1,1'-biphenyl-4-yl]sulfonyl}-L-valinate

Product 1

HCID 68714965methyl N-[(4'-{[(5-ethyl-4-hydroxy-3-methyl-1-benzofuran-2-yl)carbonyl]amino}-1,1'-biphenyl-4-yl)sulfonyl)-L-valinateYield 129.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 0.1 g (0.15 mmol) of methyl N-{[4′-({[4-(benzyloxy)-5-ethyl-3-methyl-1-benzofuran-2-yl]carbonyl}amino)-1,1′-biphenyl-4-yl]sulfonyl}-L-valinate from Example 89, dissolved in 20 mL of methanol and 10 mL of THF was added 0.2 g of 10% palladium on active carbon and the mixture was hydrogenated in a Parr hydrogenator at 40 psi for 4 hours. The reaction mixture was then filtered through celite and the celite pad was washed with with methanol. The filtrate was concentrated in vacuo to provide 0.11 g of methyl N-[(4′-{[(5-ethyl-4-hydroxy-3-methyl-1-benzofuran-2-yl)carbonyl]amino}-1,1′-biphenyl-4-yl)sulfonyl]-L-valinate. Yield ˜100%, m.p. 75-80° C. MS: 565.2 (M+H)+.

Workup

  1. filtrationThe reaction mixture was then filtered through celite
  2. washthe celite pad was washed with with methanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-01223bc7f23c446a957fbffd55acbd1b
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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