p-Toluenesulfonic acid monohydrate → HCID 10323548, compound

HRID 981282Notes

Reaction equation

HRID 981282 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:15]2[C:16]([F:42])=[CH:17][C:18]3[C:35](=[O:36])[C:34]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:33][N:20]4[CH:21]([CH2:25][O:26]C5CCCCO5)[CH2:22][O:23][C:24]=2[C:19]=34)[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:15]2[C:16]([F:42])=[CH:17][C:18]3[C:35](=[O:36])[C:34]([C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:33][N:20]4[CH:21]([CH2:25][OH:26])[CH2:22][O:23][C:24]=2[C:19]=34)[CH2:13][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11757949HCID 11757949, compound

Product 1

HCID 10323548HCID 10323548, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 2 ml of ethanol was dissolved 90 mg of ethyl 10-(1-benzyloxycarbonylaminocyclopropyl)-9-fluoro-3-(2-tetrahydropyranyloxymethyl)-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate. To the resulting solution was added 10 mg of p-toluenesulfonic acid monohydrate. The resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure. Ethanol was added to the residue obtained, and the resulting crystals were collected by filtration to obtain 47 mg (yield: 61.0%) of ethyl 10-(1-benzyloxycarbonylaminocyclopropyl)-9-fluoro-3-hydroxymethyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]-benzoxazine-6-carboxylate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionEthanol was added to the residue
  3. customobtained
  4. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-e666f7906a6f45428576d55ba6d78e87
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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