Hydrochloric Acid → HCID 136346653, compound

HRID 1971285Notes

Reaction equation

C(OC([NH:8][CH:9]([C:17](=[N:24][OH:25])[C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)[C:10]([N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])=O)(C)(C)C.Cl>CO>[NH2:8][CH:9]([C:17](=[N:24][OH:25])[C:18]1[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=1)[C:10]([N:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1)=[O:11]

Participants

Conditions

Temperature: 45 °C

Procedure

(±)-2-tert-Butyloxycarbonylamino-3-(hydroxyimino)-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-1-one TTA 08160 (100 mg, 0.29 mmol) was dissolved in MeOH (2 mL) and a solution of 1 M HCl in MeOH (1 mL, 3.00 mmol) was added and the mixture was heated for 10 min at 45° C. MeOH was evaporated and the residue was dried to give crude (±)-2-amino-3-(hydroxyimino)-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-1-one TTA 08164. Amberlite IRA-400 (Cl−) (1 mL, 1.4 mmol) was washed successively with water (2×10 mL), NaOH 0.5 N (3×20 mL), water (2×10 mL) and MeOH (3×10 mL). A solution of TTA 08164 in MeOH (30 mL) was stirred with washed Amberlite IRA-400 for 5 min at RT. After filtration, the MeOH was evaporated and the free base form was purified by column chromatography (SiO2, CH2Cl2:MeOH=9:1). HCl Treatment in MeOH gave (±)-2-amino-3-(hydroxyimino)-3-(pyridin-4-yl)-1-(pyrrolidin-1-yl)propan-1-one dihydrochloride Compound 224 (29 mg, 31% yield) as a beige solid.

Workup

customMeOH was evaporated
customthe residue was dried

Sources & evidence

ORD record: ord-cf570adb985444beb8bbf1aa5eb6d8e5
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431599B2

Reaction notes

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