Benzamide → N-[(3S,4R)-3-Hydroxy-2,2-dimethyl-6-(trifluoromethoxy)-chroman-4-yl]-2-nitrobenzamide

HRID 483751Notes

Reaction equation

[NH2:1][C@@H:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:13]([F:16])([F:15])[F:14])[CH:10]=2)[O:5][C:4]([CH3:18])([CH3:17])[C@H:3]1[OH:19].C(N(CC)CC)C.[N+:27]([C:30]1[CH:38]=[CH:37][CH:36]=[CH:35][C:31]=1[C:32](Cl)=[O:33])([O-:29])=[O:28].C(N)(=O)C1C=CC=CC=1>ClCCl>[OH:19][C@H:3]1[C@H:2]([NH:1][C:32](=[O:33])[C:31]2[CH:35]=[CH:36][CH:37]=[CH:38][C:30]=2[N+:27]([O-:29])=[O:28])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][C:13]([F:16])([F:14])[F:15])[CH:10]=2)[O:5][C:4]1([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 15 °C

Procedure

(3S,4R)-4-Amino-2,2-dimethyl-6-(trifluoromethoxy)-chroman-3-ol [prepared by the method of Quagliato et al. Biorg. & Med. Chem. Let. 1991 1, 39; (2.75 g, 10 mmol)] and triethylamine (1.39 mL, 10 mmol) were stirred together in dichloromethane (25 mL) at 0° C. To this solution was added a solution of 2-nitrobenzoylchloride (1.32 mL, 10 mmol) in dichloromethane (10 mL). The ice bath was allowed to gradually warm to 15° C. overnight. The crude benzamide was diluted with dichloromethane (50 mL), washed with water (2×10 mL), dried (MgSO4) and concentrated to afford 2.0 g (47%) of white solid: m.p. 189°-190° C.; 1H NMR (DMSO-d6): δ 9.17 (d, 1H), 8.04 (d, 1H), 7.81 (m, 2H), 7.71 (t, 1H), 7.33 (s, 1H), 7.16 (d, 1H), 6.86 (d, 1H), 5.86 (d, 1H), 4.96 (br t, 1H), 3.64 (dd, 1H), 1.42 (s, 3H), 1.19 (s, 3H).

Workup

washwashed with water (2×10 mL)
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-049b58c31cb74babb9ed19ecf0e1584f
Source dataset: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05225566

Reaction notes

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