Hydrochloric Acid → HCID 67111710, compound

HRID 1177439Notes

Reaction equation

O.[OH-].[Li+].[C:4]([C:12]1[N:17]=[C:16]2[S:18][C:19]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]4[CH2:31][CH:30]([C:32]([O:34]C)=[O:33])[CH2:29]4)=[CH:23][C:22]=3[F:36])=[N:20][C:15]2=[CH:14][CH:13]=1)(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.P([O-])([O-])([O-])=O>C1COCC1.O>[C:4]([C:12]1[N:17]=[C:16]2[S:18][C:19]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]4[CH2:31][CH:30]([C:32]([OH:34])=[O:33])[CH2:29]4)=[CH:23][C:22]=3[F:36])=[N:20][C:15]2=[CH:14][CH:13]=1)(=[O:11])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of lithium hydroxide hydrate (66.4 mg, 1582 μmol) and methyl 1-((4-(5-benzoylthiazolo[5,4-b]pyridine-2-yl)-3-fluorophenyl)methyl)azetidine-3-carboxylate (233.0 mg, 505 μmol) in THF (12.6 mL) and water (1.7 mL) was stirred at 25° C. for 1.5 h. The reaction mixture was then diluted with water (1.0 mL), acidified with 1.0N HCl (1.58 mL), brought to pH 6 with 0.05M phosphate buffer (1.0 mL), and partially concentrated in vacuo. The resulting precipitate was collected by vacuum filtration, washed with water (3.0 mL), and dried in vacuo to afford 1-((4-(5-benzoylthiazolo[5,4-b]pyridine-2-yl)-3-fluorophenyl)methyl)-azetidine-3-carboxylic acid as a colorless solid. MS (ESI) m/z: Calculated: 447.1; Observed: 448.0 (M++1).

Workup

concentrationpartially concentrated in vacuo
filtrationThe resulting precipitate was collected by vacuum filtration
washwashed with water (3.0 mL)
customdried in vacuo

Sources & evidence

ORD record: ord-9a9bdc72b38c4e02a8ed3415a13331fb
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842685B2

Reaction notes

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