(S)-1-Cyclopropyl-7-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester → (S)-7-[3-(Amino)-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester

HRID 232048Notes

Reaction equation

HRID 232048 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:28])=[C:11]([N:15]4[CH2:19][CH2:18][C@H:17]([NH:20]C(OC(C)(C)C)=O)[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:29])[C:6]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:5]2)[CH2:3][CH2:2]1>FC(F)(F)C(O)=O>[NH2:20][C@H:17]1[CH2:18][CH2:19][N:15]([C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:29])[C:6]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:5][N:4]3[CH:1]3[CH2:2][CH2:3]3)=[CH:9][C:10]=2[F:28])[CH2:16]1

Participants

3

Reactant 1

HCID 14555482(S)-1-Cyclopropyl-7-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester

Product 1

HCID 14555485(S)-7-[3-(Amino)-1-pyrrolidinyl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl esterYield 94.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 23.9 g (50 mmol) of (S)-1-cyclopropyl-7-[3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-pyrrolidinyl]-6,8-difluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid, ethyl ester in 150 ml of trifluoroacetic acid was stirred at room temperature for four hours. The solvent was removed in vacuo and the residue was triturated with 5% sodium bicarbonate. The solid was removed by filtration, washed 5% sodium bicarbonate, water and dried in vacuo to give 17.8 g of the title compound, mp 227°-228°.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was triturated with 5% sodium bicarbonate
  3. customThe solid was removed by filtration
  4. washwashed 5% sodium bicarbonate, water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-6c71886f83b546709b8e37067f8b0f7f
Source dataset
uspto-grants-1989_07
Patent number
US04851418

Reaction notes

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