L-Hydroxyproline → HCID 13136866, compound

HRID 850999Notes

Reaction equation

HRID 850999 reaction equation
[C:1]([N:4]1[CH2:11][CH2:10][CH:9](O)[C@H:5]1[C:6]([OH:8])=O)(=[O:3])[CH3:2].CN1CC[O:17]CC1.ClC(OC)=O.[NH2:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31](=[O:36])[C:30]([C:37]([OH:39])=[O:38])=[CH:29]2.C(N(CC)CC)C.Cl[Si](C)(C)C.N1C[C@H](O)C[C@H]1C(O)=O>ClCCl>[C:1]([N:4]1[CH2:11][CH:10]([OH:17])[CH2:9][CH:5]1[C:6]([NH:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31](=[O:36])[C:30]([C:37]([OH:39])=[O:38])=[CH:29]2)=[O:8])(=[O:3])[CH3:2]

Participants

9

Reactant 7

HCID 5810L-HydroxyprolineHCID 6397ChlorotrimethylsilaneHCID 6586Methyl chloroformateHCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 131063306-Amino-2-oxo-1,2-dihydroquinoline-3-carboxylic acidHCID 18595220HCID 18595220, compound

Product 1

HCID 13136866HCID 13136866, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 5.20 g (30 mmol) of N-acetyl-3-hydroxy-L-proline and 75 ml of dichloromethane is cooled to -15° and 3.3 ml (30 mmol) of N-methyl morpholine and 2.33 ml (30 mmol) methyl chloroformate is added and stirring is continued for 20 minutes at -10° to -20°. A mixture of 3.06 g (15 mmol) of 6-amino-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid, 120 ml of dichloromethane, 6.3 ml (45 mmol) of triethylamine, and 5.7 ml (45 mmol) of chlorotrimethylsilane is stirred at room temperature for 1/2 hour. The silylation mixture is cooled to -20 and the cold mixed anhydride of hydroxyproline is added and stirred for 4 hours with cooling and overnight at room temperature. The reaction mixture is evaporated to an oil which is treated with acetic acid and ethanol to yield 3.92 g of 6-[[(1-acetyl-4-hydroxy- 2-pyrrolidinyl)carbonyl]amino]-1,2-dihydro-2-oxo-3-quinolinecarboxylic acid.

Workup

  1. temperatureis cooled to -15°
  2. stirringis stirred at room temperature for 1/2 hour
  3. temperatureThe silylation mixture is cooled to -20
  4. additionis added
  5. stirringstirred for 4 hours
  6. customThe reaction mixture is evaporated to an oil which
  7. additionis treated with acetic acid and ethanol

Sources & evidence

ORD record
ord-30e5b01d8ef846f6814ef18e32718022
Source dataset
uspto-grants-1983_05
Patent number
US04382089

Reaction notes

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