Hydrochloric Acid → HCID 68766221, compound

HRID 2092718Notes

Reaction equation

[CH3:1][NH:2][CH2:3][C@@H:4]([C@H:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1.[ClH:23].C=O.C(OCC)C>CO.O.CCO.CCCCCC>[ClH:23].[CH:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:13]=[CH:14][C:5]=1[C@@H:4]1[C@@H:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[O:22][CH2:1][NH:2][CH2:3]1

Participants

Conditions

Temperature: 65 °C

Procedure

To a stirred solution of PRC200.HCl (100 mg, 0.361 mmol) dissolved in 2 mL of MeOH was added 36% aq. formaldehyde solution (0.5 mL). This solution was heated at 65° C. overnight. After rotary evaporation of the volatiles, the product was leached with diethyl ether and hexane. The crude product could be purified by converting it to a hydrochloride salt, then crystallization from a solvent mixture prepared by dissolving 5 mL of MeOH, 20 mL of diethyl ether, and 17 mL of hexane. Yield 99 mg, 95%. 1H NMR (CD3OD) δ 7.82-7.69 (m,4H), 7.63 (s, 1H), 7.48-7.39 (m,2H), 7.23 (d, J=8.1 Hz, 1H), 7.15 (s, 4H), 5.29 (d, J=9.1 Hz,1H), 5.09 (d, J=10.3 Hz, 1H), 5.02 (d, J=9.2 Hz, 1H), 3.87 (dd, J=12.2, 12.2 Hz, 1H), 3.75 (dd, J=13.0, 4.1 Hz, 1H), 3.71 (dd, J=4.1 Hz, 1H), 3.57-3.45 (m, 1H); MS: m/z (ESI) 290.11(M+1)+; [α]D20+125 (c 0.22, 9:1 EtOH:H2O).

Workup

customAfter rotary evaporation of the volatiles
customThe crude product could be purified
customcrystallization from a solvent mixture
customprepared

Sources & evidence

ORD record: ord-1f9e3bc3b67841be974c2d0751c86bd4
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440724B2

Reaction notes

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