Dichloromethane → HCID 66896394, compound

HRID 337576Notes

Reaction equation

HRID 337576 reaction equation
[CH:1]1([N:4]([CH2:12][C:13]2[CH:14]=[C:15](C=O)[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1.[CH3:25][O:26][C:27](=[O:48])[CH:28]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl[CH2:50]Cl>>[CH:1]1([N:4]([CH2:12][C:13]2[CH:14]=[C:15]([CH:50]=[CH:28][C:27]([O:26][CH3:25])=[O:48])[CH:16]=[C:17]3[C:22]=2[N:21]=[CH:20][CH:19]=[CH:18]3)[C:5]([O:6][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:11])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 86651667HCID 86651667, compound

Product 1

HCID 66896394HCID 66896394, compound

Procedure

To a solution of 1,1-dimethylethyl cyclopropyl[(6-formyl-8-quinolinyl)methyl]carbamate (1 eq.) from the previous step in dichloromethane (0.06 M) was added methyl(triphenylphosphoranylidene)acetate (1.1 eq.) at 0° C. The resulting solution was then allowed to warm slowly to RT over 4 h. The volatiles were then removed in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→3:7 (v/v) Hex:EtOAc) afforded the title compound as a white solid.

Workup

  1. customThe volatiles were then removed in vacuo
  2. customPurification of the crude product
  3. customthus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→3:7 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-8083b80603f44548a4bc611cb2dac85d
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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