Ether hydrochloride → Hydrochloric Acid

HRID 2095295Notes

Reaction equation

HRID 2095295 reaction equation
[ClH:1].CCOCC.C(OC([N:14]1[CH2:17][CH2:16][C@H:15]1[CH2:18][O:19][C:20]1[CH:21]=[C:22]([C@H:26]2[CH2:28][C@@H:27]2[CH2:29][OH:30])[CH:23]=[N:24][CH:25]=1)=O)(C)(C)C>CO>[ClH:1].[NH:14]1[CH2:17][CH2:16][C@H:15]1[CH2:18][O:19][C:20]1[CH:21]=[C:22]([C@H:26]2[CH2:28][C@@H:27]2[CH2:29][OH:30])[CH:23]=[N:24][CH:25]=1.[ClH:1]

Participants

5

Reactant 2

HCID 10953452Ether hydrochlorideHCID 68613216HCID 68613216, compound

Product 2

HCID 313Hydrochloric AcidHCID 68612460HCID 68612460, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2M anhydrous HCl/ether (2.0 mL) was added to a stirred solution of (1S,2S)-2-[5-[[1-(tert-butoxycarbonyl)-(2S)-azetidinyl]methoxy]-3-pyridyl]cyclopropylmethanol (200 mg, 0.59 mmol) in dry MeOH (2.0 mL) at 0° C. The resulting mixture was stirred at room temperature for 12 h, concentrated, and purified by HPLC to give the title compound as its hydrochloride (106 mg). 1H NMR (CD3OD, 300 MHz) δ 8.36 (s, 1H), 8.28 (s, 1H), 7.70 (s, 1H), 4.98-4.92 (m, 1H), 4.52-4.47 (m, 2H), 4.16-4.02 (m, 2H), 3.76-3.68 (m, 1H), 3.53-3.45 (m, 1H), 3.33-3.29 (m, 2H), 2.10-2.02 (m, 1H), 1.64-1.49 (m, 1H), 1.17 (t, 1H, J=7.2 Hz); MS (ESI) m/z 257 (M+Na+).

Workup

  1. concentrationconcentrated
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-2244b02aa1b64854b96ee96e3800ce7c
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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