Ethanethiol → HCID 22025328, compound

HRID 1792849Notes

Reaction equation

HRID 1792849 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1([S:11]([NH:14][CH:15]([CH2:29][C:30]2[CH:38]=[CH:37][C:36]([O:39]C)=[C:35]3[C:31]=2[CH:32]=[CH:33][NH:34]3)[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:17])(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:41][CH2:42]S.[NH4+:44].[Cl-]>>[C:5]1([S:11]([NH:14][CH2:15][C:16]([NH:18][CH2:19][CH2:20][CH:21]([C:42]2[CH:41]=[CH:37][C:36]([OH:39])=[C:35]3[C:31]=2[CH:30]=[CH:29][NH:44]3)[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:17])(=[O:12])=[O:13])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1.[C:5]1([S:11]([NH:14][CH:15]([CH2:29][C:30]2[CH:38]=[CH:37][C:36]([OH:39])=[C:35]3[C:31]=2[CH:32]=[CH:33][NH:34]3)[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:17])(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 6343Ethanethiol2×HCID 25517Ammonium ChlorideHCID 6451240Aluminum(III) Chloride2×HCID 22025339HCID 22025339, compound

Product 2

HCID 22025328HCID 22025328, compoundHCID 22025355HCID 22025355, compound

Procedure

Aluminum chloride (0.13 g, 0.99 mmol) is added to a 0° C. solution of 2-benzenesulfonylamino-3-(7-methoxy-1H-indol-4-yl)-N-(4-phenyl-butyl)-propionamide (0.12 g, 0.25 mmol) and EtSH (0.061 g, 0.99 mmol). The mixture is stirred 3.5 h while being allowed to warm to rt. Additional AlCl3 (0.13 g, 0.99 mmol) and EtSH (0.061 g, 0.99 mmol) are added and the mixture is stirred 1 h more. The mixture is then poured into a saturated NH4Cl solution and extracted twice with EtOAc. The organics are dried (MgSO4) and concentrated. The crude residue is purified by column chromatography (silica, 1:3 EtOAc/CH2Cl2) to provide the title compound 2-benzenesulfonylamino-3-(7-hydroxy-1H-indol-4-yl)-N-(4-phenyl-butyl)-propionamide as an oil.

Workup

  1. stirringthe mixture is stirred 1 h more
  2. extractionextracted twice with EtOAc
  3. dry with materialThe organics are dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude residue is purified by column chromatography (silica, 1:3 EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-1983935f784b4f378a92c5cece0120c6
Source dataset
uspto-grants-2006_07
Patent number
US07078425B2

Reaction notes

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