Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine methyl ester → methyl (2S)-2-[isobutyl(p-tolylsulfonyl)amino]-6-[[(2S)-3-phenyl-2-(p-tolylsulfonylamino)propanoyl]amino]hexanoate

HRID 1634669Notes

Reaction equation

HRID 1634669 reaction equation
[CH3:1][O:2][C:3](=[O:25])[C@H:4]([CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[N:5]([CH2:16][CH:17]([CH3:19])[CH3:18])[S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[CH2:26]1[CH2:30]O[CH2:28][CH2:27]1.[C:31]([O-:34])([O-])=O.[K+].[K+]>Cl>[CH3:28][C:27]1[CH:11]=[CH:10][C:9]([S:6]([NH:5][C@H:30]([C:31]([NH:24][CH2:23][CH2:22][CH2:21][CH2:20][C@H:4]([N:5]([S:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:16][CH:17]([CH3:18])[CH3:19])[C:3]([O:2][CH3:1])=[O:25])=[O:34])[CH2:26][C:27]2[CH:21]=[CH:20][CH:4]=[CH:3][CH:28]=2)(=[O:7])=[O:8])=[CH:30][CH:26]=1

Participants

4

Reactant 2

HCID 22975548Nalpha-isobutyl-Nalpha-(4-methylbenzenesulfonyl)-L-lysine methyl esterHCID 86626146potassium carbonate THF

Product 1

HCID 508591methyl (2S)-2-[isobutyl(p-tolylsulfonyl)amino]-6-[[(2S)-3-phenyl-2-(p-tolylsulfonylamino)propanoyl]amino]hexanoateYield 77%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a stirred solution of Nα-isobutyl-Nα-(4-methylbenzenesulfonyl)-L-lysine methyl ester (369 mg, 1 mmol, example 65, step C) in THF/K2CO3(1M) (3 mL/3 mL) was added Nα-(4-methylbenzenesulfonyl)-L-phenylalanine N-hydroxysuccinimide ester (500 mg, 1.2 mmol). The reaction mixture was stirred overnight, then diluted with 1N HCl and extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated. The crude was purified by flash chromatography using hexane/EtOAc as eluent to afford the desired product (77% yield).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude was purified by flash chromatography

Sources & evidence

ORD record
ord-56cdd1718b4541d0b6fc28d34642f1b9
Source dataset
uspto-grants-2003_01
Patent number
US06506786B2

Reaction notes

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