p-Toluenesulfonic acid monohydrate → HCID 67436943, compound

HRID 351017Notes

Reaction equation

HRID 351017 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][C@@H:19]2[C:27]([OH:29])=[O:28])(=[O:17])=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[C:31]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:31][O:28][C:27]([C@H:19]1[CH2:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:18]1[S:15]([C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)(=[O:16])=[O:17])=[O:29]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 67436128HCID 67436128, compound

Product 1

HCID 67436943HCID 67436943, compoundYield 335.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the title A compound, (R)-1-(4-benzyloxy-benzenesulfonyl)-2,3-dihydro-1H-indole-2-carboxylic acid (5.55 g, 13.6 mmol) and p-toluenesulfonic acid monohydrate (0.52 g, 2.7 mmol) in methanol (260 mL) is heated under nitrogen at reflux for 4 hours. The solution is allowed to stand overnight at room temperature which results in the formation of a crystalline solid. The crystals are collected by vacuum filtration and dried at high vacuum. A second crop of crystals is obtained from the mother liquor that is isolated and dried at high vacuum. A combined yield of 3.84 g of (R)-1-(4-benzyloxy-benzenesulfonyl)-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester is obtained as a pure crystalline product: [M+1]+=424.27.

Workup

  1. temperatureat reflux for 4 hours
  2. customwhich results in the formation of a crystalline solid
  3. filtrationThe crystals are collected by vacuum filtration
  4. customdried at high vacuum
  5. customA second crop of crystals is obtained from the mother liquor that
  6. customis isolated
  7. customdried at high vacuum

Sources & evidence

ORD record
ord-b35b91dade9945bcbeb96039875c9217
Source dataset
uspto-grants-2007_02
Patent number
US07183304B2

Reaction notes

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