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

HRID 1634641Notes

Reaction equation

HRID 1634641 reaction equation
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

Participants

6

Reactant 5

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-22b26ab669e5431e87ca0121033950b0
Source dataset
uspto-grants-2003_01
Patent number
US06506786B2

Reaction notes

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