Diethyl Ether → 2-{4-[(Tert-butoxy)carbonyl]piperazin-1-yl}-1,3-thiazole-5-carboxylic acid

HRID 1594007Notes

Reaction equation

C([O:3][C:4]([C:6]1[S:10][C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[N:8][CH:7]=1)=[O:5])C.[OH-].[K+].C(OCC)C>C(O)C>[C:4]([C:6]1[S:10][C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[N:8][CH:7]=1)([OH:5])=[O:3]

Participants

Conditions

Temperature: 40 °C

Procedure

5.33 g (15.6 mmol) of tert-butyl 4-(5-ethoxycarbonylthiazol-2-yl)piperazine-1-carboxylate [Precursor BBB60] were dissolved in ethanol together with 0.96 g (17.1 mmol) of KOH (100 ml) and stirred at 40° C. 4 h. The resulting precipitate was filtered off and dissolved in water. After this, the solution was adjusted to a pH<2 with 10% strength hydrochloric acid and extracted with chloroform. The organic phase was washed with water and a satd aq. NaCl soln and dried over MgSO4. After filtration and concentration in vacuo, 2.77 g (8.8 mmol, 56%) of tert-butyl 4-(5-carboxythiazol-2-yl)piperazine-1-carboxylate were obtained from the residue by recrystallization from diethyl ether.

Workup

custom4 h
filtrationThe resulting precipitate was filtered off
dissolutiondissolved in water
extractionextracted with chloroform
washThe organic phase was washed with water
dry with materiala satd aq. NaCl soln and dried over MgSO4
filtrationAfter filtration and concentration in vacuo

Sources & evidence

ORD record: ord-d1caa58a5b314b2aab56dca661f228d2
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07300939B2

Reaction notes

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