Pyridine → HCID 86745098, compound

HRID 728888Notes

Reaction equation

HRID 728888 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH:13]=[C:14]([CH3:26])[CH2:15][P:16]([O:22][CH:23]([CH3:25])[CH3:24])([O:18][CH:19]([CH3:21])[CH3:20])=[O:17])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=[CH:29][CH:28]=1>ClCCl.C(O)C>[CH2:28]([O:11][C:10](=[O:12])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:13]=[C:14]([CH3:26])[CH2:15][P:16]([O:22][CH:23]([CH3:25])[CH3:24])([O:18][CH:19]([CH3:20])[CH3:21])=[O:17])[CH3:29]

Participants

5

Reactant 2

HCID 1049PyridineHCID 86745097HCID 86745097, compound

Product 1

HCID 86745098HCID 86745098, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.09 g of 1-amino-1-chloro-N,N,2-trimethylpropene is added at 0°-5° to a solution of 0.2 g of acid 3 according to c) in 15ml of dry dichloromethane. After stirring for 30 minutes at 0°, 0.4 g of pyridine in 5 ml of ethanol is added. The mixture is stirred further at 0° for 90 minutes and at room temperature for 15 hours, and is then diluted with 20 ml of dichloromethane and washed twice with 20 ml of water each time. The organic phase is dried using sodium sulphate, concentrated by evaporation and chromatographed on 25 g of silica gel. Elution with ethyl acetate/ methanol 10:1 yields 0.12 g of 4. 1H-NMR(300 MHz, CDCl3): 1.2-1.4 (m, 2 (CH3)2CHO, CH3CH2O); 1.45 (s, (CH3)3CO); 1.98 (d, J=3, CH3 --C(4)); 2.55 (d, J=23, 2H--C(5)); 4.2 (m, CH3CH2O); 4.69 (m, 2 (CH3)2CHO); 5.0 (m, H--C(2)); 5.16 (m, H--C(3), NH).

Workup

  1. stirringThe mixture is stirred further at 0° for 90 minutes and at room temperature for 15 hours
  2. washwashed twice with 20 ml of water each time
  3. customThe organic phase is dried
  4. concentrationconcentrated by evaporation
  5. customchromatographed on 25 g of silica gel
  6. washElution with ethyl acetate/ methanol 10:1

Sources & evidence

ORD record
ord-5be19eed1e744ac9bfb734e925228b3b
Source dataset
uspto-grants-1991_09
Patent number
US05051413

Reaction notes

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