Methanol → HCID 10646910, compound

HRID 2253735Notes

Reaction equation

HRID 2253735 reaction equation
[C:1](/[CH:4]=[CH:5]\[C:6]1[CH:7]=[C:8]([CH2:20][C:21]([OH:23])=O)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([OH:3])=[O:2].[C:24](N1C=CN=C1)(N1C=CN=C1)=O.[CH3:36][NH:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.CO>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:36][N:37]([CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:21](=[O:23])[CH2:20][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:6](/[CH:5]=[CH:4]/[C:1]([O:3][CH3:24])=[O:2])[CH:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 11503N-MethylbenzeneethanamineHCID 682631,1'-CarbonyldiimidazoleHCID 10662890HCID 10662890, compound

Product 1

HCID 10646910HCID 10646910, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 500 mg (1.61 mmoles) of cis-3-carboxyvinyl-4-benzyloxyphenylacetic acid in 30 ml of CH2Cl2 is added 522 mg (3.22 mmoles) of 1,1'-carbonyldiimidazole (CDI). After 30 minutes, 234 ml (1.61 mmoles) of N-methyl-N-phenethylamine is added. After 18 hours a catalytic amount of 4-dimethylaminopyridine and 5 ml of methanol are added. After stirring for 21/2 hours, the reaction mixture is concentrated down in vacuo, taken up in ethyl acetate, washed with 1N NaOH, 1N HCl, H2O (2 times), brine (2 times), dried with MgSO4, filtered and concentrated in vacuo. The crude product is purified by flash chromatography to yield trans-N-methyl-N-phenethyl-2-[4-benzyloxy-3-(2-carbomethoxyvinyl)phenyl]acetamide. NMR confirms this structure which is used directly in the next step.

Workup

  1. concentrationthe reaction mixture is concentrated down in vacuo
  2. washwashed with 1N NaOH, 1N HCl, H2O (2 times), brine (2 times)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by flash chromatography

Sources & evidence

ORD record
ord-3bc8b545b55f493b8cbd23e26c77e993
Source dataset
uspto-grants-1993_08
Patent number
US05232948

Reaction notes

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