Acetonitrile → HCID 131712964, compound

HRID 1758533Notes

Reaction equation

HRID 1758533 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]1([CH2:19][O:20][P:21]([CH2:36][C:37]([OH:39])=O)([CH:23]([NH:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH3:24])=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(#N)C.[NH:43]1[CH2:57][CH2:56][CH2:55][C@H:44]1[C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46]>C(OCC)(=O)C>[C:13]1([CH2:19][O:20][P:21]([CH2:36][C:37]([N:43]2[CH2:57][CH2:56][CH2:55][C@H:44]2[C:45]([O:47][CH2:48][C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)=[O:46])=[O:39])([CH:23]([NH:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH3:24])=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 682631,1'-CarbonyldiimidazoleHCID 736155Benzyl L-prolinate2×HCID 20479544HCID 20479544, compound

Product 1

HCID 131712964HCID 131712964, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1,1'-Carbonyldiimidazole (1 g. 0.066 mole) is added to a chilled (0°) solution of the product from part (c) (2.5 g., 0.063 mole) in 40 ml. of acetonitrile. The mixture is stirred for one hour at 0°. A solution of L-proline, benzyl ester (1.3 g., 0.066 mole) in 20 ml. of acetonitrile is added. The mixture is stirred at ambient temperature for 16 hours. The solvent is removed in vacuo. The residue is dissolved in dichloromethane (125 ml.), washed with 5% potassium bisulfate, saturated sodium bicarbonate solution, brine, and dried (MgSO4). The solution is concentrated in vacuo to give an oil residue of 3.3 g. Tlc, silica gel, ethyl acetate shows a major spot at Rf 0.10. A portion (2.2 g.) is chromatographed on silica gel, eluting with ethyl acetate to give 1.7 g. of (±)-1-[(phenylmethoxy)[1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]acetyl]-L-proline, phenylmethyl ester.

Workup

  1. stirringThe mixture is stirred at ambient temperature for 16 hours
  2. customThe solvent is removed in vacuo
  3. dissolutionThe residue is dissolved in dichloromethane (125 ml.)
  4. washwashed with 5% potassium bisulfate, saturated sodium bicarbonate solution, brine
  5. dry with materialdried (MgSO4)
  6. concentrationThe solution is concentrated in vacuo
  7. customto give an oil residue of 3.3 g
  8. customA portion (2.2 g.) is chromatographed on silica gel
  9. washeluting with ethyl acetate
  10. customto give 1.7 g

Sources & evidence

ORD record
ord-96f53ce8fa504cd38de13df9d4083739
Source dataset
uspto-grants-1983_02
Patent number
US04374131

Reaction notes

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