Pyridine → HCID 69831999, compound

HRID 1937457Notes

Reaction equation

HRID 1937457 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([C@H:9]([NH:16][C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:10][C@H:11]([CH3:15])[NH:12]2)=[CH:7][C:6]=1[O:27][CH3:28])=[O:4].N1C=CC=CC=1.Cl[C:36]([O:38][CH2:39][CH3:40])=[O:37].ClC(OC)=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([C@H:9]([NH:16][C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:10][C@H:11]([CH3:15])[N:12]2[C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:7][C:6]=1[O:27][CH3:28])=[O:4]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 6586Methyl chloroformateHCID 10928Ethyl chloroformateHCID 69832790HCID 69832790, compound

Product 1

HCID 69831999HCID 69831999, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of cis-4-benzyloxycarbonylamino-6-methoxy-2-methyl-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid methyl ester (0.99 g, 2.6 mmol) in anhydrous dichloromethane (30 mL) was added pyridine (0.27 mL, 3.35 mmol). The mixture was cooled to 0° C., and ethyl chloroformate (0.29 mL, 3.1 mmol) was slowly added. The reaction was stirred at 0° C. for 30 min, then at room temperature for 2.5 h. Additional aliquots of pyridine and methyl chloroformate were added to drive the reaction to completion. The reaction mixture was evaporated to dryness, and the residue was partitioned between ethyl acetate (75 ml) and water (25 ml). The organic layer was washed with water (25 mL), dried over magnesium sulfate, filtered and concentrated in vacuo to give the crude product. Purification by silica gel chromatography using 25% ethyl acetate/hexanes as eluent afforded the title product (1.06 g). MS m/z 457 (M++1); 1H NMR (DMSO-d6) δ 1.45 (d, 3H), 6.68 (s, 1H).

Workup

  1. waitat room temperature for 2.5 h
  2. customthe reaction to completion
  3. customThe reaction mixture was evaporated to dryness
  4. customthe residue was partitioned between ethyl acetate (75 ml) and water (25 ml)
  5. washThe organic layer was washed with water (25 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give the crude product
  10. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-7f74231b95994c3e8efb17bf13932a94
Source dataset
uspto-grants-2002_05
Patent number
US06395751B1

Reaction notes

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