Hydrochloric Acid → HCID 16722381, compound

HRID 555270Notes

Reaction equation

HRID 555270 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]([N:17]1[CH2:23][C:22]3([CH3:25])[CH2:24][CH:18]1[CH2:19][C:20]([CH3:27])([CH3:26])[CH2:21]3)=[O:16])=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[CH3:25][C:22]12[CH2:24][CH:18]([N:17]([C:15]([C:11]3[CH:12]=[C:13]4[C:8](=[CH:9][CH:10]=3)[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]4)=[O:16])[CH2:23]1)[CH2:19][C:20]([CH3:27])([CH3:26])[CH2:21]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 16722380HCID 16722380, compound

Product 1

HCID 16722381HCID 16722381, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-1H-indole-2-carboxylic acid ethyl ester (500 mg, 1.35 mmol) in ethanol (10 mL) was added 1N aqueous sodium hydroxide solution (10 mL), and the resulting solution stirred for 16 h. The solution was acidified with 1N hydrochloric acid solution before the organic volatiles were removed in vacuo and the aqueous residues were extracted with DCM (3×5 mL). The combined organic phases were dried (MgSO4), filtered and evaporated in vacuo. The resulting solid was dried in vacuo at 50° C. affording 460 mg (100%) of the title compound as a solid. MS-ESI m/z 341; 1H NMR (300 MHz, DMSO-d6) δ 0.88-0.99 (m, 6H), 1.07 (d, 3H), 1.16-1.19 (m, 1H), 1.27-1.50 (m, 4H), 1.74-1.77 (m, 1H), 3.10-3.19 (m, 1H), 3.40-3.48 (m, 1H), 3.99-4.07 (m) and 4.38-4.40 (m, 1H), 7.16 (s, 1H), 7.32-7.37 (m, 1H), 7.42-7.48 (m, 1H), 7.77 (d, 1H), 11.93 (s, 1H), 13.04 (s, 1H).

Workup

  1. customwere removed in vacuo
  2. extractionthe aqueous residues were extracted with DCM (3×5 mL)
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe resulting solid was dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-4d4e4e646e754b919e6379b6b829fd15
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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