Hydrochloric Acid → HCID 71082612, compound

HRID 1620431Notes

Reaction equation

[C:1]([O:7][C:8]1[S:16][C:15]2[CH2:14][CH2:13][N:12]([C@@H:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[C:18]([O:20][CH3:21])=[O:19])[CH2:11][C:10]=2[CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].Cl>C(OCC)C>[ClH:28].[C:1]([O:7][C:8]1[S:16][C:15]2[CH2:14][CH2:13][N:12]([C@@H:17]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[C:18]([O:20][CH3:21])=[O:19])[CH2:11][C:10]=2[CH:9]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: -10 °C

Procedure

65 mg of (S)-methyl 2-(2-pivaloyloxy-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(2-chlorophenyl)-acetate (I-7) was dissolved in 4 ml of diethyl ether, and stirred in an ice-salt bath at −10° C. A hydrogen chloride saturated ethanol solution (0.2 ml) was added slowly dropwise, till the system reached about pH 2, at which a white solid was precipitated immediately. It was stirred for 5 min, allowed to stand, quickly filtered under a nitrogen atmosphere, and washed with a suitable amount of diethyl ether. The resulting solid was dried in vacuum to obtain the I-7 hydrochloride (65 mg, granular solid). Yield: 92%, melting point: 135-137° C.; 1H-NMR (300 MHz, CDCl3) δ 1.33 (s, 9H), 3.08 (s, 2H), 3.44-3.51 (m, 2H), 3.82 (s, 4H), 4.34 (s, 1H), 5.59 (s, 1H), 6.39 (s, 1H), 7.44-7.50 (m, 3H), 8.36 (d, 1H, J=7.2 Hz).

Workup

customwas precipitated immediately
stirringIt was stirred for 5 min
filtrationquickly filtered under a nitrogen atmosphere
washwashed with a suitable amount of diethyl ether
customThe resulting solid was dried in vacuum

Sources & evidence

ORD record: ord-0128817a13eb4e40868f8fe8a7524c11
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772489B2

Reaction notes

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