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

HRID 397757
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HRID 397757 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 962WaterHCID 8028Tetrahydrofuran2회HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 23552859Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine hydrochloride

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f2526fd2cc3448bea39ed463e6cdcf21
출처 데이터셋
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06610689B2

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