1,1'-Carbonyldiimidazole → HCID 54270278, compound

HRID 903450Notes

Reaction equation

HRID 903450 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([CH2:7][CH:8]([CH3:12])[C:9]([OH:11])=O)=[O:6].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:28][O:29][C:30](=[O:36])[C@@H:31]1[CH2:35][CH2:34][CH2:33][NH:32]1>O1CCCC1>[CH3:28][O:29][C:30](=[O:36])[C@@H:31]1[CH2:35][CH2:34][CH2:33][N:32]1[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7][C:5](=[O:6])[C:4]1[CH:13]=[CH:14][CH:15]=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 853477Methyl L-prolinateHCID 13563124HCID 13563124, compound

Product 1

HCID 54270278HCID 54270278, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.10 g. of 3-(4-fluorobenzoyl)-2-methylpropionic acid (Example 2) in 20 ml. of tetrahydrofuran is added 1.62 g. of 1,1'-carbonyldiimidazole. The mixture is stirred at room temperature for one hour, then 1.66 g. of L-proline methyl ester is added and stirring is continued for 18 hours. The mixture is evaporated to dryness in vacuo and the residue is partitioned between dichloromethane and water. The organic layer is separated and washed successively with 1 N hydrochloric acid, water, sodium bicarbonate solution and saline, dried over magnesium sulfate and evaporated to dryness in vacuo giving the desired product as 1.98 g. of a gum.

Workup

  1. stirringstirring
  2. waitis continued for 18 hours
  3. customThe mixture is evaporated to dryness in vacuo
  4. customthe residue is partitioned between dichloromethane and water
  5. customThe organic layer is separated
  6. washwashed successively with 1 N hydrochloric acid, water, sodium bicarbonate solution and saline
  7. dry with materialdried over magnesium sulfate
  8. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-96f23b3e552c42aa82c8e71d8e3b41ef
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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