Chlorotrimethylsilane → 7-[[(1-Acetyl-4-hydroxy-2-pyrrolidinyl)carbonyl]amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 851006Notes

Reaction equation

HRID 851006 reaction equation
[C:1]([N:4]1[CH2:11][CH:10]([OH:12])[CH2:9][C@H:5]1[C:6]([OH:8])=O)(=[O:3])[CH3:2].CN1CCOCC1.ClC(OC)=O.[NH2:25][C:26]1[CH:35]=[C:34]2[C:29]([C:30](=[O:39])[C:31]([C:36]([OH:38])=[O:37])=[CH:32][NH:33]2)=[CH:28][CH:27]=1.C(N(CC)CC)C.Cl[Si](C)(C)C>ClCCl>[C:1]([N:4]1[CH2:11][CH:10]([OH:12])[CH2:9][CH:5]1[C:6]([NH:25][C:26]1[CH:35]=[C:34]2[C:29]([C:30](=[O:39])[C:31]([C:36]([OH:38])=[O:37])=[CH:32][NH:33]2)=[CH:28][CH:27]=1)=[O:8])(=[O:3])[CH3:2]

Participants

8

Reactant 6

HCID 6397ChlorotrimethylsilaneHCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 2729005(2S)-1-acetyl-4-hydroxypyrrolidine-2-carboxylic acidHCID 102623227-Amino-4-hydroxyquinoline-3-carboxylic acid

Product 1

HCID 205034397-[[(1-Acetyl-4-hydroxy-2-pyrrolidinyl)carbonyl]amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acidYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 6.41 g (37 mmol) of N-acetyl-4-hydroxy-L-proline, 4.07 ml (37 mmol) of N-methyl morpholine, 2.87 ml (37 mmol) of methyl chloroformate, and 90 ml of dichloromethane is stirred at -10° to -20° for 30 minutes. A mixture of 4.08 g (20 mmol) of 7-amino-1, 4-dihydro-4-oxo-3-quinolinecarboxylic acid, 8.4 ml (60 mmol) of triethylamine, 7.6 ml (60 mmol) of chlorotrimethylsilane, and 100 ml of dichloromethane is stirred at room temperature for 30 minutes and then is cooled to -30°. The cold mixed anhydride is added to the cold silylated quinoline and is stirred with cooling for 4 hours and overnight at room temperature. The reaction mixture is evaporated to dryness and the residue is treated with water and 1 N hydrochloric acid. The solid is filtered to give 5.30 g of 7-[[(1-acetyl-4-hydroxy-2-pyrrolidinyl)carbonyl]amino]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.

Workup

  1. stirringis stirred at room temperature for 30 minutes
  2. temperatureis cooled to -30°
  3. stirringis stirred
  4. customThe reaction mixture is evaporated to dryness
  5. additionthe residue is treated with water and 1 N hydrochloric acid
  6. filtrationThe solid is filtered

Sources & evidence

ORD record
ord-c1a3671b4810440c8520bc1197997e17
Source dataset
uspto-grants-1983_05
Patent number
US04382089

Reaction notes

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