Triethylamine → (4-phenylphenyl)-methyl-N-[(2R*,3R*)-2-isopropyl-4-oxo-oxetan-3-yl]-carbamate

HRID 530561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 530561
O[C@H](C(C)C)[C@@H](N([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)C(OC)=O)C(O)=O.O[C@@H:28]([CH:50]([CH3:52])[CH3:51])[C@@H:29]([N:33]([C:38]1C=CC(C2C=CC=CC=2)=CC=1)[C:34]([O:36]C)=[O:35])[C:30]([OH:32])=[O:31].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[C:18]1([C:15]2[CH:14]=[CH:13][C:12]([O:36][C:34](=[O:35])[N:33]([CH3:38])[C@H:29]3[C:30](=[O:32])[O:31][C@@H:28]3[CH:50]([CH3:52])[CH3:51])=[CH:17][CH:16]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86700003(2R*,3S*)-3-hydroxy-4-methyl-2-[(4-phenylphenyl)-methoxy-carbonylamino]-pentanoic acidHCID 86700005(2R*,3R*)-3-hydroxy-4-methyl-2-[(4-phenylphenyl)-methoxy-carbonylamino]-pentanoic acid

Produkt 1

HCID 86700004(4-phenylphenyl)-methyl-N-[(2R*,3R*)-2-isopropyl-4-oxo-oxetan-3-yl]-carbamateAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Under nitrogen atmosphere, to a stirred mixture of (2R*,3R*)-3-hydroxy-4-methyl-2-[(4-phenylphenyl)-methoxy-carbonylamino]-pentanoic acid and (2R*,3S*)-3-hydroxy-4-methyl-2-[(4-phenylphenyl)-methoxy-carbonylamino]-pentanoic acid (0.059 g, 0.17 mmol) in dry CH2Cl2 (7.0 mL), at 0° C., Et3N (0.07 mL, 0.5 mmol) and subsequently TBTU (0.065 g, 0.2 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 90:10 to 80:20) to afford the pure title compound (0.01 g, 17%), as pure anti diastereoisomer, as white solid. MS (ESI) m/z: 357 [M−NH4]+; (ESI) m/z: 338 [M−H]−. 1H NMR (DMSO-d6) δ 0.89 (d, J=6.79 Hz, 3H), 0.97 (d, J=6.57 Hz, 3H), 1.81-2.12 (m, 1H), 4.26 (dd, J=4.38, 9.11 Hz, 1H), 4.80 (dd, J=4.39, 8.16 Hz, 1H), 5.12 (s, 2H), 7.29-7.54 (m, 5H), 7.63-7.77 (m, 4H), 8.26 (d, J=8.21 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-df59dc5ddb564a8a817c8c6d24b5f5b1
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353075B2

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