Ethanol → (S)-3-[[[2-phthalimido-3-phenylpropyl]ethoxyphosphinyl]amino]-2-oxo-1-piperidineacetic acid, ethyl ester

HRID 484764Notes

Reaction equation

HRID 484764 reaction equation
[C:1]1(=[O:24])[N:5]([CH:6]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][P:8](=[O:11])([OH:10])O)[C:4](=[O:19])[C:3]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:2]12.P(Cl)(Cl)(Cl)(Cl)Cl.[CH2:31](O)[CH3:32].C(N(CC)CC)C.[NH2:41][C@H:42]1[CH2:47][CH2:46][CH2:45][N:44]([CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[C:43]1=[O:54]>C1C=CC=CC=1.C(Cl)Cl>[C:4]1(=[O:19])[N:5]([CH:6]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][P:8]([NH:41][C@H:42]2[CH2:47][CH2:46][CH2:45][N:44]([CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])[C:43]2=[O:54])([O:10][CH2:31][CH3:32])=[O:11])[C:1](=[O:24])[C:2]2=[CH:23][CH:22]=[CH:21][CH:20]=[C:3]12

Participants

8

Reactant 5

HCID 702EthanolHCID 8471TriethylamineHCID 24819Phosphorus pentachlorideHCID 13556450(S)-3-Amino-2-oxo-1-piperidineacetic acid, Ethyl esterHCID 13556465(2-Phthalimido-3-phenylpropyl)phosphonic acid

Product 1

HCID 86740219(S)-3-[[[2-phthalimido-3-phenylpropyl]ethoxyphosphinyl]amino]-2-oxo-1-piperidineacetic acid, ethyl ester

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of (2-phthalimido-3-phenylpropyl)phosphonic acid in dry benzene is treated with phosphorus pentachloride and stirred at room temperature under argon for an hour. The mixture is then refluxed for 15 minutes, cooled and evaporated to dryness at room temperature (0.5 mm. of Hg). The residue is taken up in dry methylene chloride and reacted successively with a mixture of ethanol (1 eq.) and triethylamine (1 eq.) in methylene chloride and (S)-3-amino-2-oxopiperidineacetic acid, ethyl ester according to the procedure of Example 1(g). Work up of the reaction mixture according to the procedure of Example 1(g) yields (S)-3-[[[2-phthalimido-3-phenylpropyl]ethoxyphosphinyl]amino]-2-oxo-1-piperidineacetic acid, ethyl ester.

Workup

  1. temperatureThe mixture is then refluxed for 15 minutes
  2. temperaturecooled
  3. customevaporated to dryness at room temperature (0.5 mm. of Hg)

Sources & evidence

ORD record
ord-cc8e8cf0aed04f81b2a93892c5523969
Source dataset
uspto-grants-1985_08
Patent number
US04533661

Reaction notes

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