m-Chloroperbenzoic acid → HCID 14320482, compound

HRID 712096Notes

Reaction equation

ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([O:19][C:20]([NH:22][C@H:23]1[C@@H:28]([C:29]([O:31][CH3:32])=[O:30])[CH2:27][CH:26]=[CH:25][CH2:24]1)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[CH2:12]([O:19][C:20]([NH:22][C@@H:23]1[CH2:24][C@H:25]2[C@H:26]([O:9]2)[CH2:27][C@@H:28]1[C:29]([O:31][CH3:32])=[O:30])=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

m-Chloroperbenzoic acid (5.56 g, 32.2 mmol) was added to a solution of methyl (1S,6R)-6-{[(benzyloxy)carbonyl]amino}cyclohex-3-ene-1-carboxylate (7.8 g, 27 mmol) in methylene chloride (150 mL) with stirring at about 0° C. The mixture was slowly warmed to room temperature and stirred overnight. The mixture was diluted with dichloromethane then washed with sat. NaHCO3 (3×). The organic layer was dried (MgSO4), filtered, and concentrated. The crude was purified on silica gel, eluted with 0-50% EtOAc in hexanes to give 4.7 g (57%) of the desired product as a white solid. LCMS calculated for C16H20NO5 (M+H)+: m/z=306.1. Found: 306.0. 1H NMR (300 MHz, CDCl3) δ 7.37-7.29 (m, 5H), 5.75 (d, J=9.9 Hz, 1H), 5.04 (s, 2H), 4.09 (dtd, J=14.0, 6.8, 6.0, and 3.2 Hz, 1H), 3.65 (s, 3H), 3.18 (d, J=5.9 Hz, 2H), 2.60 (dd, J=15.5 and 7.3 Hz, 1H), 2.48 (td, J=7.3, 6.6, and 3.2 Hz, 1H), 2.23-2.01 (m, 3H) ppm.

Workup

temperatureThe mixture was slowly warmed to room temperature
stirringstirred overnight
washthen washed with sat. NaHCO3 (3×)
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe crude was purified on silica gel
washeluted with 0-50% EtOAc in hexanes

Sources & evidence

ORD record: ord-df524d31018a49478148a828b57eee83
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181271B2

Reaction notes

Loading…