Hydrochloric Acid → HCID 71082614, compound

HRID 1620432Notes

Reaction equation

[CH3:1][C:2]([CH3:29])([CH2:27][CH3:28])[C:3]([O:5][C:6]1[S:14][C:13]2[CH2:12][CH2:11][N:10]([C@@H:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[C:16]([O:18][CH3:19])=[O:17])[CH2:9][C:8]=2[CH:7]=1)=[O:4].Cl>C(OCC)C>[ClH:26].[CH3:1][C:2]([CH3:29])([CH2:27][CH3:28])[C:3]([O:5][C:6]1[S:14][C:13]2[CH2:12][CH2:11][N:10]([C@@H:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])[C:16]([O:18][CH3:19])=[O:17])[CH2:9][C:8]=2[CH:7]=1)=[O:4]

Participants

Conditions

Temperature: -10 °C

Procedure

65 mg of (S)-methyl 2-(2-(2,2-dimethylbutanoyloxy)-6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)-2-(2-chlorophenyl)-acetate (I-8) 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, then 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-8 hydrochloride (60 mg, white granular solid). Yield: 88%, melting point: 133-135° C.; 1H-NMR (300 MHz, CDCl3) δ 0.91 (t, 3H, J=7.6 Hz), 1.29 (s, 6H), 1.69 (q, 2H, J=7.4 Hz), 3.08 (s, 1H), 3.48 (m, 2H), 3.83 (s, 4H), 4.35 (s, 1H), 5.59 (s, 1H), 6.37 (s, 1H), 7.44-7.50 (m, 3H), 8.36 (d, 1H, J=6.84 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-41dd4c43d787440fbd87b5b898fae79c
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772489B2

Reaction notes

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