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Water → (2S)-2-[isobutyl(p-tolylsulfonyl)amino]-6-[[(2S)-3-phenyl-2-(p-tolylsulfonylamino)propanoyl]amino]hexanoic acid

HRID 1634641
ノート
印刷プレビュー

反応式

HRID 1634641 の反応式
Cl.[CH2:2]([N:6]([S:16]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C@H:7]([C:13]([OH:15])=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])[CH:3]([CH3:5])[CH3:4].[OH-:26].[Na+].[OH2:28].CCO[C:32]([CH3:34])=[O:33].[CH2:35]1[CH2:39]O[CH2:37][CH2:36]1>>[CH3:37][C:36]1[CH:21]=[CH:20][C:19]([S:16]([NH:6][C@H:34]([C:32]([NH:12][CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]([N:6]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:2][CH:3]([CH3:4])[CH3:5])[C:13]([OH:15])=[O:14])=[O:33])[CH2:39][C:35]2[CH:4]=[CH:3][CH:2]=[CH:37][CH:36]=2)(=[O:28])=[O:26])=[CH:39][CH:35]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 962WaterHCID 8028Tetrahydrofuran2 回HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 23552859Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine hydrochloride

生成物 1

HCID 508526(2S)-2-[isobutyl(p-tolylsulfonyl)amino]-6-[[(2S)-3-phenyl-2-(p-tolylsulfonylamino)propanoyl]amino]hexanoic acid
収率 76%

実験手順

A suspension of Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-L-lysine hydrochloride (600 mg) in THF (20 mL) was treated with a 1N NaOH (1.5 mL) to pH 10. A solution of commercially available Nα-(4-methylbenzenesulfonyl)-L-phenylalanine acid chloride (250 mg) in dry THF (20 mL) was added to the suspension and stirred for 2 h. Afterwards, water (2 mL) was added resulting in a clear solution. The reaction mixture was stirred for 12 h. Then, EtOAc (30 mL) was added and the organic phase was washed with 1N HCl. The organic phase was removed. Evaporation of the solvent gave a crude product which was triturated with ether to yield 750 mg (76%) of the title compound.

後処理

  1. customresulting in a clear solution
  2. stirringThe reaction mixture was stirred for 12 h
  3. washthe organic phase was washed with 1N HCl
  4. customThe organic phase was removed
  5. customEvaporation of the solvent
  6. customgave a crude product which
  7. customwas triturated with ether

出典と根拠

ORDレコード
ord-22b26ab669e5431e87ca0121033950b0
出典データセット
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06506786B2

反応ノート

読み込み中…

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