Triethylamine → ARN 077 (enantiomer)

HRID 530522Notes

Reaction equation

O[C@H:2]([CH3:22])[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[CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Under nitrogen atmosphere at 0° C., to a stirred mixture of (2S,3R)-3-hydroxy-2-(5-phenylpentoxy-carbonylamino)-butanoic acid (0.3 g, 0.89 mmol) in dry CH2Cl2 (30 mL), Et3N (0.37 mL, 2.67 mmol) and subsequently TBTU (0.34 g, 1.06 mmol) were added. The mixture was left stirring 1 h at 0° C. and 15 h at rt. Upon full conversion of the starting material, the organics were removed under reduced pressure, and the resulting crude product absorbed over silica gel and purified by typical column chromatography, eluting with Cy:EtOAc (from 100:0 to 0:100) to afford the title compound (0.18 g, 70%), as white solid. [α]25D +21.3 (c 0.1, CHCl3). MS (ESI) m/z: 292 [M−H]+; (ESI) m/z: 290 [M−H]−. 1H NMR (DMSO-d6) δ 1.37-1.28 (m, 2H), 1.33 (d, J=6.4 Hz, 3H), 1.64-1.53 (m, 4H), 2.57 (t, J=7.7 Hz, 2H), 4.06-3.93 (m, 2H), 4.84 (dq, J=6.1, 6.4 Hz, 1H), 5.40 (dd, J=6.1, 9.4 Hz, 1H), 7.30-7.13 (m, 5H), 8.19 (d, J=9.4 Hz, 1H).

Workup

additionwere added
waitThe mixture was left
customUpon full conversion of the starting material, the organics were removed under reduced pressure
customthe resulting crude product absorbed over silica gel
custompurified by typical column chromatography
washeluting with Cy

Sources & evidence

ORD record: ord-4113fcc675324834b2220aab6c74e5f9
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353075B2

Reaction notes

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