Water → HCID 508724, compound

HRID 397806Notes

Reaction equation

HRID 397806 reaction equation
[K+].[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:22][CH:23]([CH3:25])[CH3:24])[C@H:13]([C:19]([O-:21])=[O:20])[CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[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:4]=[CH:5][C:6]([S:9]([NH:12][C@H:32]([C:30]([NH:18][CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]([N:12]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([NH2:2])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[CH2:22][CH:23]([CH3:25])[CH3:24])[C:19]([OH:21])=[O:20])=[O:31])[CH2:37][C:33]2[CH:3]=[CH:8][CH:7]=[CH:35][CH:34]=2)(=[O:10])=[O:26])=[CH:37][CH:33]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 131723746HCID 131723746, compound

Product 1

HCID 508724HCID 508724, compoundYield 4.6%

Procedure

A suspension of Nα-(4-aminobenzenesulfonyl)-Nα-isobutyl-L-lysine potassium salt (190 mg, 0.5 mmol, example 166, step B) in THF (10 mL) was treated with a solution of Nα-(4-methylbenzenesulfonyl)-L-phenylalanine acid chloride (187 mg, 0.5 mmol) in dry THF (10 mL). The suspension was 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 15 mg (4.6%) 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-391b64bba8f7473c88cee5c67bc3292c
Source dataset
uspto-grants-2003_08
Patent number
US06610689B2

Reaction notes

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