Water → HCID 508723, compound

HRID 396923Notes

Reaction equation

HRID 396923 reaction equation
[C:1]1([S:7]([N:10]([CH2:20][CH:21]([CH3:23])[CH3:22])[C@H:11]([C:17]([OH:19])=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[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:3]=[CH:2][C:1]([S:7]([NH:10][C@H:32]([C:30]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]([N:10]([S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:9])=[O:8])[CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]([OH:19])=[O:18])=[O:31])[CH2:37][C:33]2[CH:6]=[CH:5][CH:4]=[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 69348042HCID 69348042, compound

Product 1

HCID 508723HCID 508723, compoundYield 6%

Procedure

A suspension of Nα-benzenesulfonyl-Nα-isobutyl-L-lysine (150 mg, 0.5 mmol), in THF (10 mL) was treated with a 1N NaOH (3.0 mL) to pH 10. A solution of commercially available Nα-(4-methylbenzenesulfonyl)-L-phenylalanine acid chloride (187 mg, 0.5 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 19 mg (6%) 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-79b64445b5b44711aa6ac1f0d3f4b5d9
Source dataset
uspto-grants-2003_08
Patent number
US06608100B1

Reaction notes

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