Triphenylphosphine → 1-[(2,2-dimethylethoxy)carbonyl]-(cis)-4-[4-(2-methoxyethenyl)phenoxy]-L-proline, diphenylmethyl ester
Reaction equation
[CH3:1][CH:2]([CH3:29])[CH2:3][O:4][C:5]([N:7]1[CH2:27][C@H:26]([OH:28])[CH2:25][C@H:8]1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:49][O:50][CH:51]=[CH:52][C:53]1[CH:58]=[CH:57][C:56](O)=[CH:55][CH:54]=1>C1C=CC=CC=1>[CH3:1][CH:2]([CH3:29])[CH2:3][O:4][C:5]([N:7]1[CH2:27][C@@H:26]([O:28][C:56]2[CH:57]=[CH:58][C:53]([CH:52]=[CH:51][O:50][CH3:49])=[CH:54][CH:55]=2)[CH2:25][C@H:8]1[C:9]([O:11][CH:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:10])=[O:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 1-[(2,2-dimethylethoxy)carbonyl]-(trans)-4-hydroxy-L-proline, diphenylmethyl ester, triphenylphosphine, and 4-(2-methoxyethenyl)phenol is taken up in benzene and evaporated to dryness. The residue is dissolved in dry tetrahydrofuran, cooled to -10° under argon, and treated with diethylazodicarboxylate. The reaction mixture is worked up according to the procedure of Example 1(b) to yield 1-[(2,2-dimethylethoxy)carbonyl]-(cis)-4-[4-(2-methoxyethenyl)phenoxy]-L-proline, diphenylmethyl ester.
Workup
- customevaporated to dryness
- dissolutionThe residue is dissolved in dry tetrahydrofuran
- temperaturecooled to -10° under argon
- additiontreated with diethylazodicarboxylate
Sources & evidence
- ORD record
- ord-8980026a705e4fcd9c2d5f90a66b9b94
- Source dataset
- uspto-grants-1985_08
- Patent number
- US04536501
Reaction notes
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