Sulfuric Acid → HCID 18659612, compound

HRID 1608518Notes

Reaction equation

HRID 1608518 reaction equation
[CH:1]([CH:3]([NH:8][C:9](=[O:26])[C@H:10]([CH2:22][CH:23]([CH3:25])[CH3:24])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:4][CH2:5][CH2:6][CH3:7])=O.Cl.[NH2:28][CH2:29][CH2:30][SH:31].C(N(CC)CC)C.S(=O)(=O)(O)O>CO>[S:31]1[CH2:30][CH2:29][NH:28][CH:1]1[CH:3]([NH:8][C:9](=[O:26])[C@H:10]([CH2:22][CH:23]([CH3:25])[CH3:24])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8471TriethylamineHCID 9082Cysteamine HydrochlorideHCID 455774117591-20-5

Product 1

HCID 18659612HCID 18659612, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 20 ml of methanol was dissolved 1.0 g of N-benzyloxycarbonyl-L-leucine-(1-formyl)pentylamide obtained in the same manner as in Example 4-(b), and 400 mg of 2-aminoethanethiol hydrochloride, 0.4 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 redueed pressure. The residue was purified by medium-pressure column chromatography on silica gel to obtain 1.2 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 redueed pressure
  4. customThe residue was purified by medium-pressure column chromatography on silica gel

Sources & evidence

ORD record
ord-fcedd6051ce744d499b9ab2e19979d61
Source dataset
uspto-grants-1995_03
Patent number
US05395824

Reaction notes

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