Sulfuric Acid → HCID 15228360, compound

HRID 1608523Notes

Reaction equation

HRID 1608523 reaction equation
[CH:1]([CH:3]([NH:8][C:9](=[O:19])[C@H:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[NH:11][C:12](=[O:14])[CH3:13])[CH2:4][CH2:5][CH2:6][CH3:7])=O.[NH2:20][CH2:21][CH2:22][SH:23].C(N(CC)CC)C.S(=O)(=O)(O)O>CO>[S:23]1[CH2:22][CH2:21][NH:20][CH:1]1[CH:3]([NH:8][C:9](=[O:19])[C@H:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[NH:11][C:12](=[O:14])[CH3:13])[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6058CysteamineHCID 8471TriethylamineHCID 15228355HCID 15228355, compound

Product 1

HCID 15228360HCID 15228360, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 20 ml of methanol was dissolved 2.0 g of N-acetyl-L-leucine-(1-formyl)pentylamide obtained in the same manner as in Example 16-(c), and 800 mg of 2-aminoethanethiol, 1.0 ml of triethylamine, and a catalytic amount of concentrated sulfuric acid were added thereto. The mixture was allowed to react at room temperature for 12 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue was purified by medium-pressure column chromatography on silica gel to obtain 1.8 g of the titled compound as a colorless crystal.

Workup

  1. customto react at room temperature for 12 hours
  2. customAfter completion of the reaction
  3. customthe solvent was removed by distillation under reduced pressure
  4. customthe residue was purified by medium-pressure column chromatography on silica gel

Sources & evidence

ORD record
ord-16cb4b4ef1ff44faa8ce7c1a9376e8e7
Source dataset
uspto-grants-1995_03
Patent number
US05395824

Reaction notes

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