4-Toluenesulfonyl chloride → 2,3-Dioxoindoline-5-sulfonyl chloride

HRID 2191221

반응식

HRID 2191221 반응식
O(CC1CCCN1[S:14]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[C:20]2=[O:27])(=[O:16])=[O:15])C1C=CC=CC=1.N1C2C(=CC(S(O)(=O)=O)=CC=2)C(=O)C1=O.[Na].P(Cl)(Cl)([Cl:46])=O.C(N1C=CC=C1CO)(OC(C)(C)C)=O.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C1S(=O)(=O)CCC1.N1C=CC=CC=1>[Cl:46][S:14]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21](=[O:26])[C:20]2=[O:27])(=[O:16])=[O:15]

참가 물질

9

반응물 6

HCID 73974-Toluenesulfonyl chlorideHCID 24813Phosphorus oxychlorideHCID 817492,3-Dioxo-5-indolinesulfonic acidHCID 5360545SodiumHCID 10512124tert-Butyl 2-(hydroxymethyl)-1H-pyrrole-1-carboxylateHCID 186720675-(2-Phenoxymethylpyrrolidine-1-sulfonyl)isatin

생성물 1

HCID 159089472,3-Dioxoindoline-5-sulfonyl chloride

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 31347Sulfolane용매

실험 절차

The synthesis of 5-(2-phenoxymethylpyrrolidine-1-sulfonyl)isatin analogues is shown in Scheme 1 (FIG. 5). The 5-chlorosulfonylisatin 6 was prepared by reaction of 5-isatinsulfonic acid, sodium salt hydrate (5) with phosphorus oxychloride in tetramethylene sulfone at 60° C. for 3 h. The hydroxyl group of N-Boc-2-pyrrolmethanol (7) was first tosylated with p-toluenesulfonyl chloride in pyridine to give compound 8, followed by displacement of the tosylate group by sodium phenoxide in DMF to afford N-Boc-2-(phenoxymethyl)pyrrolidine 9. The N-Boc group of 9 was removed with TFA, and the secondary amine was coupled with 6 in THF using triethylamine as an acid scavenger to afford the 5-(2-phenoxymethyl-pyrrolidinesulfonyl)-1H-2,3-dione 10 in 84% yield. The isatin nitrogen was alkylated by treatment of 10 with sodium hydride in DMF at 0° C. followed by addition of various alkyl halides to give compounds 2 and 11a-e,g-i. Compound 11f was prepared by hydrolysis of 11e with sodium hydroxide in aqueous methanol.

출처 및 근거

ORD 기록
ord-305c4cc19ce1473fb7cc60ab56a03d31
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329686B2

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