Citric Acid → 2-{1-[(Tert-butoxy)carbonyl]piperidin-4-yl}-1,3-oxazole-4-carboxylic acid

HRID 2043727

Reaction equation

C[O:2][C:3]([C:5]1[N:6]=[C:7]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)[O:8][CH:9]=1)=[O:4].O.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.[Cl-].[Na+].C(OCC)C>[C:3]([C:5]1[N:6]=[C:7]([CH:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)[O:8][CH:9]=1)([OH:4])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

1,1-Dimethylethyl 4-[4-(methoxycarbonyl)-2-oxazolyl]-1-piperidinecarboxylate (i.e. the product of Example 7, Step C) (1.41 g, 4.55 mmol) was dissolved in 12 mL tetrahydrofuran, and 8 mL of water was added. The reaction mixture was cooled to 0° C. with vigorous stirring. A 1 N aqueous sodium hydroxide solution (9.1 mL) was added dropwise, and the reaction mixture was stirred at room temperature for 2 h. The mixture was diluted with saturated sodium chloride solution (10 mL), 30 mL of diethyl ether was added and the aqueous phase was acidified to pH 3-4 by dropwise addition of 20% citric acid solution. The precipitated solid was filtered and dried to give 1.21 g of the title compound.

Workup

additionwas added
filtrationThe precipitated solid was filtered
customdried

Sources & evidence

ORD record: ord-f1443203cad24280ad03f35ceefb7173
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586611B2

Linked notes

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