Acetonitrile → HCID 131712965, compound

HRID 1758534Notes

Reaction equation

HRID 1758534 reaction equation
[C:1]1([CH2:7][O:8][P:9]([CH2:26][C:27](O)=[O:28])([CH:11]([NH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(#N)C.[NH:33]1[CH2:47][CH2:46][CH2:45][C@H:34]1[C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36]>C(OCC)(=O)C>[C:1]1([CH2:7][O:8][P:9]([CH2:26][C:27]([N:33]2[CH2:47][CH2:46][CH2:45][C@H:34]2[C:35]([O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[O:36])=[O:28])([CH:11]([NH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6342Acetonitrile2×HCID 736155Benzyl L-prolinate2×HCID 13101400HCID 13101400, compound

Product 1

HCID 131712965HCID 131712965, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1,1-Carbonyldiimidazole (1.8 g., 0.011 mole) is added to a chilled (0°) solution of the product from part (c) (4.6 g., 0.011 mole) in 50 ml. of acetonitrile. The mixture is stirred for one hour at 0° and a solution of L-proline, benzyl ester (2.3 g., 0.011 mole) in 25 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 200 ml. of dichloromethane, washed with 5% potassium bisulfate, saturated sodium bicarbonate solution, brine, and dried (MgSO4). The solvent is removed in vacuo to give an oil residue of 6.5 g. Tlc, silica gel, ethyl acetate, shows a major spot at Rf 0.50 visualized with PMA. The residue is chromatographed on silica gel, eluted with dichloromethane/ethyl acetate (9:1) and (4:1) to give 5.4 g. of (±)-1-[(phenylmethoxy)[1-[(ethoxycarbonyl)amino]-3-phenylpropyl]phosphinyl]acetyl]-L-proline, phenylmethyl ester. Tlc shows a single spot at Rf 0.50.

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 200 ml
  4. washof dichloromethane, washed with 5% potassium bisulfate, saturated sodium bicarbonate solution, brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent is removed in vacuo
  7. customto give an oil residue of 6.5 g
  8. customThe residue is chromatographed on silica gel
  9. washeluted with dichloromethane/ethyl acetate (9:1) and (4:1)
  10. customto give 5.4 g

Sources & evidence

ORD record
ord-61f6072154524cd7aa47c55011450405
Source dataset
uspto-grants-1983_02
Patent number
US04374131

Reaction notes

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