D-1,4-Dithiothreitol → N-butanesulfonyl-tryptophanamide hydrochloride

HRID 1941338Notes

Reaction equation

HRID 1941338 reaction equation
[CH2:1]([S:5]([NH:8][C:9](=[O:29])[C@H:10]([CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)[NH:11]C(OC(C)(C)C)=O)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].SC[C@H]([C@@H](CS)O)O.[ClH:38].O1CCOCC1>O1CCOCC1>[ClH:38].[CH2:1]([S:5]([NH:8][C:9](=[O:29])[C@H:10]([CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)[NH2:11])(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 446094D-1,4-DithiothreitolHCID 204431481,4-Dioxane hydrochlorideHCID 70092293HCID 70092293, compound

Product 1

HCID 70092888N-butanesulfonyl-tryptophanamide hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-butanesulfonyl-(t-butoxycarbonyl)tryptophanamide (0.71 g, 1.68 mmol) and dithiothreitol (47 mg, 0.3 mmol) in 1,4-dioxane (4 ml) is added 4N HCl/1,4-dioxane (20 ml) at more temperature under nitrogen atmosphere and the mixture is stirred for 18 hours. The reaction mixture is concentrated in vacuo and the solid residue is washed with diethyl ether and dried to give N-butanesulfonyl-tryptophanamide hydrochloride.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. washthe solid residue is washed with diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-b63a79babe574752a44940013a096e30
Source dataset
uspto-grants-1997_12
Patent number
US05703106

Reaction notes

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