Triphenylphosphine → (cis)-4-[4-(2-methoxyethenyl)phenoxy]-1-[[(3-ethoxy-3-oxopropyl)ethylamino]carbonyl]-L-proline, phenylmethyl ester

HRID 485331Notes

Reaction equation

HRID 485331 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][CH2:6][N:7]([CH2:26][CH3:27])[C:8]([N:10]1[CH2:24][C@H:23]([OH:25])[CH2:22][C@H:11]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:9])[CH3:2].[CH3:29][O:30][CH:31]=[CH:32][C:33]1[CH:38]=[CH:37][C:36](O)=[CH:35][CH:34]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>>[CH3:29][O:30][CH:31]=[CH:32][C:33]1[CH:38]=[CH:37][C:36]([O:25][C@@H:23]2[CH2:24][N:10]([C:8]([N:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:28])[CH2:26][CH3:27])=[O:9])[C@H:11]([C:12]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[O:13])[CH2:22]2)=[CH:35][CH:34]=1

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 541301084-(2-Methoxyethenyl)phenolHCID 131714305(trans)-1-[[(3-Ethoxy-3-oxopropyl)ethylamino]carbonyl]-4-hydroxy-L-proline, phenylmethyl ester

Product 1

HCID 131714306(cis)-4-[4-(2-methoxyethenyl)phenoxy]-1-[[(3-ethoxy-3-oxopropyl)ethylamino]carbonyl]-L-proline, phenylmethyl ester

Procedure

Equimolar amounts of (trans)-1-[[(3-ethoxy-3-oxopropyl)ethylamino]carbonyl]-4-hydroxy-L-proline, phenylmethyl ester and 4-(2-methoxyethenyl)phenol are reacted in the presence of triphenylphosphine and diethylazodicarboxylate to give (cis)-4-[4-(2-methoxyethenyl)phenoxy]-1-[[(3-ethoxy-3-oxopropyl)ethylamino]carbonyl]-L-proline, phenylmethyl ester.

Sources & evidence

ORD record
ord-0851be4a195641449d20ec9c03817185
Source dataset
uspto-grants-1985_08
Patent number
US04536501

Reaction notes

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