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Hydrochloric Acid → Diphenylmethyl [4-[3-(4-thiocarbamoylbenzenesulfonylamino)propyl]-2,3-dioxopiperazin-1-yl]acetate

HRID 1417228
Notes
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Reaction equation

HRID 1417228 reaction equation
[SH2:1].[C:2]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:25])[C:19](=[O:40])[C:18]2=[O:41])(=[O:12])=[O:11])=[CH:6][CH:5]=1)#[N:3].C(N(CC)CC)C.Cl>O.C(OCC)(=O)C.N1C=CC=CC=1>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]([O:26][CH:27]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:25])[C:19](=[O:40])[C:18]2=[O:41])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[S:1])[NH2:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 54344221Diphenylmethyl [4-[3-(4-cyanobenzenesulfonylamino)propyl]-2,3-dioxopiperazin-1-yl]acetate

Product 1

HCID 54290528Diphenylmethyl [4-[3-(4-thiocarbamoylbenzenesulfonylamino)propyl]-2,3-dioxopiperazin-1-yl]acetate

Reagents, catalysts & solvents

3
HCID 962WaterSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Hydrogen sulfide gas was introduced into a mixture of 0.48 g of diphenylmethyl [4-[3-(4-cyanobenzenesulfonylamino) propyl]-2,3-dioxopiperazin-1-yl ]-acetate, 2.4 ml of triethylamine and 4.8 ml of pyridine at room temperature until the mixture was saturated therewith. After stirring at the same temperature for 5 hours, the reaction mixture was added to a mixed solvent of 30 ml of ethyl acetate and 30 ml of water, and the pH was adjusted to 4 with 6N hydrochloric acid. The organic layer was separated and the aqueous layer was re-extracted with 10 ml of ethyl acetate. The combined organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The resulting residue was purified by a silica gel column chromatography (eluent; chloroform: methanol=20:1) to obtain 0.40 g of diphenylmethyl [4-[3-(4-thiocarbamoylbenzenesulfonylamino) propyl]-2,3-dioxopiperazin-1-yl]acetate as yellow crystals.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was re-extracted with 10 ml of ethyl acetate
  3. washThe combined organic layer was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe resulting residue was purified by a silica gel column chromatography (eluent; chloroform: methanol=20:1)

Sources & evidence

ORD record
ord-da5702b5c111406ea1c3f8b69a6a64d4
Source dataset
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05877174

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes