Methanol → 2-(3-((5-Cyclopropyl-3-(2-phenylcyclopropyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6 carboxylic acid

HRID 1748212Notes

Reaction equation

HRID 1748212 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([CH:9]3[CH2:11][CH:10]3[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[CH2:18][O:19][CH:20]2[CH2:26][CH:25]3[N:27]([C:28]4[S:29][C:30]5[CH:36]=[C:35]([C:37]([O:39]CC)=[O:38])[CH:34]=[CH:33][C:31]=5[N:32]=4)[CH:22]([CH2:23][CH2:24]3)[CH2:21]2)[CH2:3][CH2:2]1.CO.O.[Li+].[OH-]>C1COCC1>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([CH:9]3[CH2:11][CH:10]3[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:5]=2[CH2:18][O:19][CH:20]2[CH2:26][CH:25]3[N:27]([C:28]4[S:29][C:30]5[CH:36]=[C:35]([C:37]([OH:39])=[O:38])[CH:34]=[CH:33][C:31]=5[N:32]=4)[CH:22]([CH2:23][CH2:24]3)[CH2:21]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 67983333Ethyl 2-(3-((5-cyclopropyl-3-(2-phenylcyclopropyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6-carboxylate

Product 1

HCID 679838932-(3-((5-Cyclopropyl-3-(2-phenylcyclopropyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6 carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of ethyl 2-(3-((5-cyclopropyl-3-(2-phenylcyclopropyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6-carboxylate (0.03 g, 0.05 mmol) in THF:MeOH:H2O=3:2:1 solution (0.6 mL) was treated with 6N LiOH (0.05 mL) at rt for 14 h. The volatiles were removed in vacuo, the residue diluted with water (1 mL), and 6N HCl was added to adjust pH to 2. The solids were collected by filtration and dried under vacuum to afford 2-(3-((5-cyclopropyl-3-(2-phenylcyclopropyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6 carboxylic acid as hydrochloride salt.

Workup

  1. customThe volatiles were removed in vacuo
  2. additionthe residue diluted with water (1 mL), and 6N HCl
  3. additionwas added
  4. filtrationThe solids were collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-3199d94823834edf84b0b85f1bf604c1
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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