1,4-Dioxane → HCID 53838529, compound

HRID 850629Notes

Reaction equation

HRID 850629 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH2:7][C@H:8]([NH:18][CH2:19][CH2:20][NH:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Br:31])[N:26]=1)[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([O:15][CH2:16][CH3:17])[CH:14]=1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.Cl[C:43](OC1C=CC([N+]([O-])=O)=CC=1)=[O:44].O1CCOCC1>ClCCl.CCOC(C)=O>[C:1]([O:5][C:6](=[O:32])[CH2:7][C@H:8]([N:18]1[CH2:19][CH2:20][N:21]([CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Br:31])[N:26]=2)[C:43]1=[O:44])[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([O:15][CH2:16][CH3:17])[CH:14]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 54098783HCID 54098783, compound

Product 1

HCID 53838529HCID 53838529, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 20-10 (0.80 g, 1.57 mmol) and diisopropylethylamine (0.823 mL, 4.72 mmol) in dichloromethane (10 mL) at 0° C. was added p-nitrophenyl chloroformate (0.333 g, 1.65 mmol). The solution stirred for 30 minutes and dioxane (10 mL) was added, then refluxed for 4 hours. EtOAc (100 mL) was added and the organics were washed with 10% K2CO3, dried, and concentrated in vacuo. The residue was chromatographed (silica gel, [70:20:10 CHCl3 /EtOAc/MeOH]) to give 20-11.

Workup

  1. temperaturerefluxed for 4 hours
  2. washthe organics were washed with 10% K2CO3
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed (silica gel, [70:20:10 CHCl3 /EtOAc/MeOH])
  6. customto give 20-11

Sources & evidence

ORD record
ord-8e1d25ade8d3418b9dd6cfb07db5cc4d
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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