Acetic Anhydride → HCID 10366131, compound

HRID 1090112Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([NH:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=O)(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C>>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:18]=[CH:19][C:20]([S:23]([N:26]3[CH2:27][CH2:28][CH2:29][C:30]3=[O:32])(=[O:25])=[O:24])=[CH:21][CH:22]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 517045Sodium Acetate

HCID 10479429HCID 10479429, compound

Product 1

HCID 10366131HCID 10366131, compoundYield 71.1%

Procedure

8.2 g of product obtained in Stage A, 8.2 g of sodium acetate and 123 cm3 of acetic anhydride are heated to reflux for 30 minutes. The mixture is cooled to ambient temperature, evaporated to dryness, the residue is taken up with 100 cm3 of water, filtered and dried. 5.6 g of 1-[4-(4-benzyloxycarbonylpiperazin-1-yl)phenylsulphonyl]-2-pyrrolidinone is obtained. m.p.=153°-155° C. After recrystallization from an ethanol-acetone mixture (10-1), 3.7 g of product is obtained, melting at 158°-160° C. 7 g of product prepared as above and 1 g of palladium are put in suspension in 105 cm3 of dimethylacetamide, a few drops of triethylamine are added, then the whole is hydrogenated under ambient pressure (with 280 cm3 of hydrogen). The catalyst is filtered off, evaporated to dryness and 2 g of product is obtained which is dissolved in acetic acid and evaporated to dryness. The residue is taken up in isopropyl alcohol and 1.5 g of crystallized product is obtained.

Workup

temperatureto reflux for 30 minutes
customevaporated to dryness
filtrationfiltered
customdried

Sources & evidence

ORD record: ord-e550673df96244fdb9909a2ea529efb7
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05081130

Reaction notes

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