Chlorotrimethylsilane → 6-[[(1-Acetyl-2-pyrrolidinyl)carbonyl]-amino]-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid

HRID 850998Notes

Reaction equation

HRID 850998 reaction equation
[C:1]([N:4]1[CH2:11][CH2:10][CH2:9][C@H:5]1[C:6]([OH:8])=O)(=[O:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33](=[O:38])[C:32]([C:39]([OH:41])=[O:40])=[CH:31]2.C(N(CC)CC)C.Cl[Si](C)(C)C.N1CCC[C@H]1C(O)=O>ClCCl>[C:1]([N:4]1[CH2:11][CH2:10][CH2:9][CH:5]1[C:6]([NH:27][C:28]1[CH:29]=[C:30]2[C:35](=[CH:36][CH:37]=1)[NH:34][C:33](=[O:38])[C:32]([C:39]([OH:41])=[O:40])=[CH:31]2)=[O:8])(=[O:3])[CH3:2]

Participants

9

Reactant 7

HCID 6397ChlorotrimethylsilaneHCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 66141N-Acetyl-L-prolineHCID 145742L-ProlineHCID 131063306-Amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acid

Product 1

HCID 131368646-[[(1-Acetyl-2-pyrrolidinyl)carbonyl]-amino]-1,2-dihydro-2-oxo-3-quinolinecarboxylic acidYield 64.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4.71 g (30 mmol) of N-acetyl-L-proline and 60 ml of dichloromethane is cooled to -18° and 3.3 ml (30 mmol) of N-methyl morpholine and 3.9 ml (30 mmol) of isobutyl chloroformate is added, and the reaction mixture is stirred for 30 minutes at -10° to -20°. A mixture of 4.08 g (20 mmol) of 6-amino-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid, 150 ml of dichloromethane, 8.4 ml (60 mmol) of triethylamine, and 7.6 ml (60 mmol) of chlorotrimethylsilane is stirred at room temperature for 35 minutes. The silylation mixture is cooled to -20° and the mixed anhydride of proline is added and stirred with cooling overnight. The reaction mixture is evaporated to dryness, and the residue is treated with ethanol to yield 4.42 g of 6-[[(1-acetyl-2-pyrrolidinyl)carbonyl]-amino]-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid, mp 303° dec.

Workup

  1. stirringis stirred at room temperature for 35 minutes
  2. temperatureThe silylation mixture is cooled to -20°
  3. stirringstirred
  4. temperaturewith cooling overnight
  5. customThe reaction mixture is evaporated to dryness
  6. additionthe residue is treated with ethanol

Sources & evidence

ORD record
ord-f517b170a6ef4c969b8511f3ac9afc36
Source dataset
uspto-grants-1983_05
Patent number
US04382089

Reaction notes

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