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

HRID 29332
ノート
印刷プレビュー

反応式

HRID 29332 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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)−.

後処理

  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

出典と根拠

ORDレコード
ord-97a1cdc7fe414f2288ca5ed81a450565
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07420001B2

反応ノート

読み込み中…

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