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

HRID 1417228ノート

反応式

HRID 1417228 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-da5702b5c111406ea1c3f8b69a6a64d4
出典データセット
uspto-grants-1999_03
特許番号
US05877174

反応ノート

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