1,1'-Carbonyldiimidazole → [Bis(2-propenyloxy)phosphinyl]Acetyl-L-Proline, tert-Butyl Ester

HRID 26651Notes

Reaction equation

HRID 26651 reaction equation
[CH2:1]([O:4][P:5]([CH2:11][C:12]([OH:14])=O)([O:7][CH2:8][CH:9]=[CH2:10])=[O:6])[CH:2]=[CH2:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[C:27]([O:31][C:32](=[O:38])[C@@H:33]1[CH2:37][CH2:36][CH2:35][NH:34]1)([CH3:30])([CH3:29])[CH3:28]>C(#N)C>[CH2:8]([O:7][P:5]([CH2:11][C:12]([N:34]1[CH2:35][CH2:36][CH2:37][C@H:33]1[C:32]([O:31][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:38])=[O:14])([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 21321956[Bis(2-propenyloxy)phosphinyl]acetic acid

Product 1

HCID 131711484[Bis(2-propenyloxy)phosphinyl]Acetyl-L-Proline, tert-Butyl Ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

[Bis(2-propenyloxy)phosphinyl]acetic acid (7.0 g., 0.032 mol.) is dissolved in 200 ml. of acetonitrile and stirred in an ice bath under a drying tube. 1,1'-Carbonyldiimidazole (5.5 g., 0.032 mol.) is then added and the mixture is stirred for 45 minutes. L-Proline t-butyl ester (5.5 g., 0.032 mol.) is then added, the ice bath removed, and the mixture stirred overnight. The solution is then evaporated in vacuo and the residue taken up in ethyl acetate and washed with 5% potassium bisulfate, saturated sodium bicarbonate, and brine, then dried (MgSO4) and evaporated to a viscous liquid (10.7 g., 89%). The product [Bis(2-propenyloxy)phosphinyl]acetyl-L-proline, tert-butyl ester is substantially pure by tlc (Rf =0.35, silica gel, ethyl acetate; several trace impurities).

Workup

  1. customthe ice bath removed
  2. stirringthe mixture stirred overnight
  3. customThe solution is then evaporated in vacuo
  4. washwashed with 5% potassium bisulfate, saturated sodium bicarbonate, and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to a viscous liquid (10.7 g., 89%)

Sources & evidence

ORD record
ord-2005f6d85121413fae0cafbb1a7a5926
Source dataset
uspto-grants-1979_04
Patent number
US04151172

Reaction notes

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