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

HRID 530566Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-4ca48d91e80b4460b3e4324d911734cb
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353075B2

Reaction notes

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