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

HRID 530547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530547
O[C@H:2]([CH2:22][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].O[C@@H](CC)[C@@H](NC(OCCCCCC1C=CC=CC=1)=O)C(O)=O.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[CH2:22][CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86699983(2R*,3S*)-3-hydroxy-2-(5-phenylpentoxy-carbonylamino)-pentanoic acidHCID 86699985(2R*,3R*)-3-hydroxy-2-(5-phenylpentoxy-carbonylamino)-pentanoic acid

Produkt 1

HCID 866999845-phenylpentyl-N-[(2R*,3R*)-2-ethyl-4-oxo-oxetan-3-yl]-carbamateAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under nitrogen atmosphere, to a stirred mixture of (2R*,3R*)-3-hydroxy-2-(5-phenylpentoxy-carbonylamino)-pentanoic acid and (2R*,3S*)-3-hydroxy-2-(5-phenylpentoxy-carbonylamino)-pentanoic acid (0.155 g, 0.48 mmol) in dry CH2Cl2, (20.0 mL), at 0° C., Et3N (0.2 mL, 1.44 mmol) and subsequently TBTU (0.185 g, 0.58 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 title compound (0.075 g, 57%), as pure anti diastereoisomer, as white solid. MS (ESI) m/z: 323 [M−NH4]+; (ESI) m/z: 304 [M−H]−. 1H NMR (DMSO-d6) δ 0.90 (t, J=7.41 Hz, 3H), 1.26-1.38 (m, 2H), 1.58 (p, J=7.71, 8.27 Hz, 4H), 1.67-1.90 (m, 2H), 2.57 (t, J=7.65 Hz, 2H), 3.98 (t, J=6.60 Hz, 2H), 4.51 (td, J=4.28, 6.84 Hz, 1H), 4.69 (dd, J=4.32, 8.12 Hz, 1H), 7.09-7.32 (m, 5H), 8.06 (d, J=8.09 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-7b8c817d05634a45b17fe150c4a2a0b9
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353075B2

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