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Triethylamine → 5-phenylpentyl-N-[(2S*,3R*)-2-isopropyl-4-oxo-oxetan-3-yl]-carbamate

HRID 530566
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 530566
O[C@H:2]([CH:22]([CH3:24])[CH3:23])[C@H:3]([NH:7][C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:9])[C:4]([OH:6])=[O:5].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:8](=[O:9])[NH:7][C@H:3]2[C:4](=[O:6])[O:5][C@H:2]2[CH:22]([CH3:24])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86700008(2S*,3R*)-3-hydroxy-4-methyl-2-(5-phenylpentoxy-carbonylamino)-pentanoic acid

Produkt 1

HCID 867000095-phenylpentyl-N-[(2S*,3R*)-2-isopropyl-4-oxo-oxetan-3-yl]-carbamateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under nitrogen atmosphere, to a stirred mixture of (2S*,3R*)-3-hydroxy-4-methyl-2-(5-phenylpentoxy-carbonylamino)-pentanoic acid (0.14 g, 0.43 mmol) in dry CH2Cl2 (20 mL), at 0° C., Et3N (0.18 mL, 1.3 mmol) and subsequently TBTU (0.17 g, 0.55 mmol) were added. The mixture was left stirring at 0° C. for 1 h and at rt for 15 h. The organics were then removed under reduced pressure, and the resulting crude product purified by column chromatography, using a Teledyne ISCO apparatus, eluting with Cy:AcOEt (from 100:0 to 80:20) to afford the pure title compound (0.052 g, 40%), as pure syn diastereoisomer, as a white solid. MS (ESI) m/z: 337 [M−NH4]+; (ESI) m/z: 318 [M−H]−. 1H NMR (DMSO-d6) δ 0.75 (d, J=6.57 Hz, 3H), 0.96 (d, J=6.51 Hz, 3H), 1.25-1.39 (m, 2H), 1.52-1.65 (m, 4H), 2.03 (dt, J=6.53, 10.83 Hz, 1H), 2.57 (t, J=7.67 Hz, 2H), 4.01 (t, J=6.58 Hz, 2H), 4.24 (dd, J=5.92, 10.84 Hz, 1H), 5.44 (dd, J=5.92, 9.53 Hz, 1H), 7.13-7.34 (m, 5H), 8.27 (d, J=9.52 Hz, 1H).

Aufarbeitung

  1. waitThe mixture was left
  2. customThe organics were then removed under reduced pressure
  3. customthe resulting crude product purified by column chromatography
  4. washeluting with Cy

Quellen und Nachweise

ORD-Eintrag
ord-4ca48d91e80b4460b3e4324d911734cb
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09353075B2

Notizen zur Reaktion

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