p-Toluenesulfonic acid → HCID 86737764, compound

HRID 1680017Notes

Reaction equation

HRID 1680017 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([CH:11]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[N:10]3[C:22](=[O:44])[CH:23]([NH:24]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C@H:9]3[S:8]2)[CH2:4][CH2:3]1.[C:45]1([CH3:55])[CH:50]=[CH:49][C:48]([S:51]([OH:54])(=[O:53])=[O:52])=[CH:47][CH:46]=1>CC(C)=O>[C:45]1([CH3:55])[CH:46]=[CH:47][C:48]([S:51]([OH:54])(=[O:52])=[O:53])=[CH:49][CH:50]=1.[C:45]1([CH3:55])[CH:46]=[CH:47][C:48]([S:51]([OH:54])(=[O:52])=[O:53])=[CH:49][CH:50]=1.[NH2:24][CH:23]1[C:22](=[O:44])[N:10]2[CH:11]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[C:5]3([S:8][C@H:9]12)[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 70575048HCID 70575048, compound

Product 1

HCID 86737764HCID 86737764, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 16 g (0.0266 mole) of benzyl 1'-methyl-6-tritylamino-spiro-[pename-2,4'-piperidine]-3-carboxylate (obtained in 7.1) and of 10.12 g (0.053 mole) of p-toluene-sulfonic acid is stirred for four hours at ambient temperature in 160 ml of acetone. After filtration and drying, 15 g (79.9% yield) of benzyl 6-amino-1'-methyl-spiro[penam-2,4'-piperidine]-3-carboxylate di-p-toluenesulfonate are obtained; M.P. 182°-183° C.

Workup

  1. filtrationAfter filtration
  2. customdrying

Sources & evidence

ORD record
ord-6c2ded7989f64174850e815e0d4ad35b
Source dataset
uspto-grants-1981_06
Patent number
US04271172

Reaction notes

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