Hydrochloric Acid → HCID 13561946, compound

HRID 1249045Notes

Reaction equation

HRID 1249045 reaction equation
C([NH:3][C:4]1[CH:29]=[CH:28][C:7]([CH2:8][S:9][C:10]([N:12]2[C@@H:24]([C:25]([OH:27])=[O:26])[CH2:23][C:22]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][C:14]=3[CH2:13]2)=[S:11])=[CH:6][CH:5]=1)=O.C(O)(=O)CS.Cl>C(O)C>[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][S:9][C:10]([N:12]2[C@@H:24]([C:25]([OH:27])=[O:26])[CH2:23][C:22]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][C:14]=3[CH2:13]2)=[S:11])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1133Thioglycolic AcidHCID 13936960HCID 13936960, compound

Product 1

HCID 13561946HCID 13561946, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3R)-2-[(4-(Formylamino)benzylthio)thiocarbonyl]-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (1.46 g) is dissolved in ethanol (34 ml) and thereto is added thioglycolic acid (0.04 ml) and is further added dropwise 6N HCl (34 ml). The mixture is stirred under argon stream for 2.5 hours and then distilled under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=94:5:1-20:10:1) to give the title compound (0.52 g), as pale yellow powder.

Workup

  1. distillationdistilled under reduced pressure
  2. customto remove the solvent
  3. customThe residue is purified by silica gel column chromatography (solvent, chloroform:methanol:acetic acid=94:5:1-20:10:1)

Sources & evidence

ORD record
ord-b6bffaff51944cbdbd753d7add7192c6
Source dataset
uspto-grants-1986_12
Patent number
US04628057

Reaction notes

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