1,1'-Carbonyldiimidazole → (S)-4-Hydroxy-1-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-L-proline, methyl ester

HRID 851428Notes

Reaction equation

[CH2:1]([O:3][P:4]([CH2:16][C:17]([OH:19])=O)([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[OH:32][CH:33]1[CH2:37][NH:36][C@H:35]([C:38]([O:40][CH3:41])=[O:39])[CH2:34]1>C(#N)C.C(OCC)(=O)C>[OH:32][CH:33]1[CH2:37][N:36]([C:17](=[O:19])[CH2:16][P:4]([O:3][CH2:1][CH3:2])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:5])[C@H:35]([C:38]([O:40][CH3:41])=[O:39])[CH2:34]1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of [ethoxy(4-phenylbutyl)phosphinyl]acetic acid (1.71 g), acetonitrile and carbonyldiimidazole (0.97 g) is stirred under argon at 0° C. for 1 hour. (S)-4-hydroxyproline, methyl ester (0.006 mole) is suspended in acetonitrile, added to the mixture and stirred at room temperature 90 minutes. Solvent is stripped off, and the resulting oil is taken up in ethyl acetate, washed with 5% potassium bisulfate, washed with saturated sodium bicarbonate, washed with brine, dried over magnesium sulfate, and the solvent stripped to leave 2.23 g of the title compound as an oil.

Workup

additionadded to the mixture
stirringstirred at room temperature 90 minutes
washwashed with 5% potassium bisulfate
washwashed with saturated sodium bicarbonate
washwashed with brine
dry with materialdried over magnesium sulfate

Sources & evidence

ORD record: ord-ad446060ec5a469e8acd81a6f6b1b0ca
Source dataset: uspto-grants-1983_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04384123

Reaction notes

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