4-Toluenesulfonyl chloride → HCID 86735448, compound

HRID 127900Notes

Reaction equation

[OH:1][CH2:2][C@H:3]1[C@@H:6]([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:9][C:8]2=[O:24])[C:5](=[O:25])[N:4]1CC1C=CC(OC)=CC=1OC.[S:37](Cl)([CH3:40])(=[O:39])=[O:38].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>>[S:37]([O:1][CH2:2][C@H:3]1[C@@H:6]([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:9][C:8]2=[O:24])[C:5](=[O:25])[NH:4]1)(=[O:39])(=[O:38])[CH3:40]

Participants

Reactant 3

HCID 73974-Toluenesulfonyl chloride

HCID 31297Methanesulfonyl chloride

HCID 70578463HCID 70578463, compound

Product 1

HCID 86735448HCID 86735448, compoundYield 73%

Procedure

When cis-2-hydroxymethyl-1-(2,4-dimethoxybenzyl)-3-(4,5-diphenyl-2-oxo-4-oxazolin-3-yl)-4-oxoazetidine is reacted according to Example 13 except that mesyl chloride is substituted for p-toluenesulfonyl chloride, cis-3-(4,5-diphenyl-2-oxo-4-oxazolin-3-yl)-4-oxo-2-azetidinylmethyl mesylate is obtained; 73% yield, mp 185°-8° from ethyl acetate-hexane.

Sources & evidence

ORD record: ord-26a97918c0914d51a65aca169909db0a
Source dataset: uspto-grants-1981_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04257947

Reaction notes

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