p-Toluenesulfonic acid → HCID 86737760, compound

HRID 1680018Notes

Reaction equation

HRID 1680018 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][C:10]3([CH:16]([C:17]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:18])[N:15]4[C:27](=[O:49])[CH:28]([NH:29]C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[C@H:14]4[S:13]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:50]1([CH3:60])[CH:55]=[CH:54][C:53]([S:56]([OH:59])(=[O:58])=[O:57])=[CH:52][CH:51]=1>CC(C)=O>[C:50]1([CH3:60])[CH:51]=[CH:52][C:53]([S:56]([OH:59])(=[O:57])=[O:58])=[CH:54][CH:55]=1.[C:50]1([CH3:60])[CH:51]=[CH:52][C:53]([S:56]([OH:59])(=[O:57])=[O:58])=[CH:54][CH:55]=1.[NH2:29][CH:28]1[C:27](=[O:49])[N:15]2[CH:16]([C:17]([O:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])[C:10]3([S:13][C@H:14]12)[CH2:11][CH2:12][N:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:8][CH2:9]3

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 70577387HCID 70577387, compound

Product 1

HCID 86737760HCID 86737760, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.33 g (0.002 mole) of benzyl 1'-phenyl-6-tritylamino-spiro [penam-2,4'-piperidine]-3-carboxylate (obtained in 7.3) and 0.76 g of p-toluenesulfonic acid in 10 ml of acetone is stirred at ambient temperature for 6 hours. After filtering and drying, there is obtained 1.40 g of benzyl 6-amino-1'-phenyl-spiro[penam-2,4'-piperidine]-3-carboxylate di-p-toluenesulfonate. Yield: 92%; M.P. 168°-169° C. (decomposition).

Workup

  1. filtrationAfter filtering
  2. customdrying

Sources & evidence

ORD record
ord-82e5c9f40d344e999ca516be25426ed9
Source dataset
uspto-grants-1981_06
Patent number
US04271172

Reaction notes

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