Pyridine → HCID 86745098, compound

HRID 1682318Notes

Reaction equation

HRID 1682318 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 15 ml 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-b74288b114fd48bdb7e1350eaa83490c
Source dataset
uspto-grants-1992_12
Patent number
US05175344

Reaction notes

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