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Hydrochloric Acid → (1S,2S)-2-{[(benzyloxy)carbonyl]amino}-1-methyl-3-oxo-3-[(3-oxopropyl)amino]propyl myristate

HRID 25707
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 25707
[C:1]([O:16][C@@H:17]([CH3:42])[C@H:18]([NH:31][C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[C:19]([NH:21][CH2:22][CH2:23][CH:24](OCC)[O:25]CC)=[O:20])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].Cl.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:1]([O:16][C@@H:17]([CH3:42])[C@H:18]([NH:31][C:32]([O:34][CH2:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:33])[C:19](=[O:20])[NH:21][CH2:22][CH2:23][CH:24]=[O:25])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]
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Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 69752788(1S,2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(3,3-diethoxypropyl)amino]-1-methyl-3-oxopropyl myristate

Produkt 1

HCID 86587939(1S,2S)-2-{[(benzyloxy)carbonyl]amino}-1-methyl-3-oxo-3-[(3-oxopropyl)amino]propyl myristateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of (1S,2S)-2-{[(benzyloxy)carbonyl]amino}-3-[-(3,3-diethoxypropyl)amino]-1-methyl-3-oxopropyl myristate (1.06 g, 1.79 mmol, obtained from Reference Example 47) in anhydrous tetrahydrofuran was added 0.5 N hydrochloric acid (4.3 ml). The resulting solution was stirred at room temperature for 5 hours. The reaction mixture was brought to pH 9 with aqueous sodium bicarbonate, extracted with ethyl acetate (3×75 ml), the combined organics were washed with saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed (flash column, silica gel, 45% ethyl acetate in hexane) to provide (1S,2S)-2-{[(benzyloxy)carbonyl]amino}-1-methyl-3-oxo-3-[(3-oxopropyl)amino]propyl myristate (694 mg, 75%) as a white solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×75 ml)
  2. washthe combined organics were washed with saturated sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed (flash column, silica gel, 45% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2e8aeb90799945a6988b9be021129abb
Quelldatensatz
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06858591B2

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