p-Toluenesulfonic acid → HCID 66649236, compound

HRID 419786Notes

Reaction equation

HRID 419786 reaction equation
[NH2:1][C:2]1[C:7](=[O:8])[N:6]([C@@H:9]2[O:31][C@H:30]([CH2:32][O:33][C:34](=[O:41])[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@@H:20]([O:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C@H:10]2[O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5](=[O:42])[NH:4][C:3]=1[NH2:43].[CH3:44]C1C=CC(S(O)(=O)=O)=CC=1>C(OC(OCC)OCC)C>[C:12]([O:11][C@@H:10]1[C@H:20]([O:21][C:22](=[O:29])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C@@H:30]([CH2:32][O:33][C:34](=[O:41])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[O:31][C@H:9]1[N:6]1[C:7](=[O:8])[C:2]2[NH:1][CH:44]=[N:43][C:3]=2[NH:4][C:5]1=[O:42])(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66649411HCID 66649411, compound

Product 1

HCID 66649236HCID 66649236, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 31214Ethyl orthoformateSolvent

Procedure

A mixture of 50 (4.30 g, 7.33 mmol), TsOH (catalytic amount), and triethylorthoformate (90 mL) was stirred at room temperature for 24 hr, concentrated, and the residue purified on a silica gel column (CHCl3:MeOH=30:1 v/v) to give compound 51 (2.20 g, 50%).

Workup

  1. concentrationconcentrated
  2. customthe residue purified on a silica gel column (CHCl3:MeOH=30:1 v/v)

Sources & evidence

ORD record
ord-7ebbc465f67e47daa11a6daffbf38dc2
Source dataset
uspto-grants-2012_01
Patent number
US08093380B2

Reaction notes

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