Water → HCID 508577, compound

HRID 1634660Notes

Reaction equation

HRID 1634660 reaction equation
Cl.[CH2:2]([N:6]([S:16]([C:19]1[S:20][CH:21]=[CH:22][CH:23]=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-:24].[Na+].[OH2:26].CCO[C:30]([CH3:32])=[O:31].[CH2:33]1[CH2:37]O[CH2:35][CH2:34]1>>[CH3:35][C:34]1[CH:22]=[CH:23][C:19]([S:16]([NH:6][C@H:32]([C:30]([NH:12][CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]([N:6]([S:16]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)(=[O:18])=[O:17])[CH2:2][CH:3]([CH3:5])[CH3:4])[C:13]([OH:15])=[O:14])=[O:31])[CH2:37][C:33]2[CH:4]=[CH:3][CH:2]=[CH:35][CH:34]=2)(=[O:26])=[O:24])=[CH:37][CH:33]=1

Participants

6

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 69348712HCID 69348712, compound

Product 1

HCID 508577HCID 508577, compoundYield 57%

Procedure

A suspension of Nα-isobutyl-Nα-(2-thiophenesulfonyl)-L-lysine hydrochloride (150 mg, 0.5 mmol), in THF (20 mL) was treated with a 1N NaOH (0.5 mL) to pH 10. A solution of commercially available Nα-(4-methylbenzenesulfonyl)-L-phenylalanine acid chloride (150 mg, 0.4 mmol), in dry THF (10 mL) was added to the suspension and stirred for 4 h. Afterwards, water (2 mL) was added resulting in a clear solution. 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 purified by preparative HPLC to yield 150 mg (57%) of the title compound.

Workup

  1. customresulting in a clear solution
  2. washthe organic phase was washed with 1N HCl
  3. customThe organic phase was removed
  4. customEvaporation of the solvent
  5. customgave a crude product which
  6. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-71b7b7b843a146e293c29f36f9e41844
Source dataset
uspto-grants-2003_01
Patent number
US06506786B2

Reaction notes

Loading…