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

HRID 1285474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1285474
[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

Komponenten

8

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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 to 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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-abca0688543644e49758f332ba7561a1
Quelldatensatz
uspto-grants-1986_01
Patentnummer
US04567167

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