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

HRID 1859179Notes

Reaction equation

HRID 1859179 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]([O:15][CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[C:8](=[O:29])[C:7]1=[O:30].[C:31]([C:33]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1)#[N:32].C(N(CC)CC)C.Cl>O1CCCC1.O.C(OCC)(=O)C>[C:31]([C:33]1[CH:34]=[CH:35][C:36]([S:39]([NH:2][CH2:3][CH2:4][CH2:5][N:6]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]([O:15][CH:16]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:14])[C:8](=[O:29])[C:7]2=[O:30])(=[O:41])=[O:40])=[CH:37][CH:38]=1)#[N:32]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chlorideHCID 67554632Diphenylmethyl [4-(3-aminopropyl)-2,3-dioxopiperazin-1-yl]acetate hydrochloride

Product 1

HCID 54344221Diphenylmethyl [4-[3-(4-cyanobenzenesulfonylamino)propyl]-2,3-dioxopiperazin-1-yl]acetateYield 47.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 7 ml of tetrahydrofuran was dissolved 0.70 g of diphenylmethyl [4-(3-aminopropyl)-2,3-dioxopiperazin-1-yl]acetate hydrochloride, and 0.36 g of 4-cyanobenzenesulfonyl chloride and then 0.58 ml of triethylamine were added thereto under ice-cooling. After stirring at room temperature for 30 minutes, the reaction mixture was added to a mixed solvent of 20 ml of ethyl acetate and 20 ml of water and the pH was adjusted to 3 with 2N hydrochloric acid. The organic layer was separated, washed with water and then a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=20:1) to obtain 0.43 g of diphenylmethyl [4-[3-(4-cyanobenzenesulfonylamino)propyl]-2,3-dioxopiperazin-1-yl]acetate as a yellow foamy substance.

Workup

  1. temperatureunder ice-cooling
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-8c9f7064354b4016975379443ce41f1a
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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