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

HRID 745346Notes

Reaction equation

HRID 745346 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-d00d017d5d254a08a38a19cc31a2b878
Source dataset
uspto-grants-1986_07
Patent number
US04598071

Reaction notes

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