Sodium Hydroxide → HCID 45487115, compound

HRID 2354882Notes

Reaction equation

HRID 2354882 reaction equation
[OH-].[Na+].C([O:5][C:6]([CH:8]1[CH2:18][CH:17]2[N:19]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:10]([CH2:11][C:12]3[NH:13][N:14]=[CH:15][C:16]=32)[CH2:9]1)=[O:7])C>C1COCC1>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([N:19]2[CH:10]3[CH2:9][CH:8]([C:6]([OH:7])=[O:5])[CH2:18][CH:17]2[C:16]2[CH:15]=[N:14][NH:13][C:12]=2[CH2:11]3)(=[O:22])=[O:21])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 16045395HCID 16045395, compound

Product 1

HCID 45487115HCID 45487115, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (0.5 mL, 3 N solution) was added to a solution 12-(4-chloro-benzenesulfonyl)-4,5,12-triaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene-10-carboxylic acid ethyl ester (321 mg, 0.783 mmol) in THF (2 mL). The resulting mixture was stirred at room temperature for 4 h. The reaction mixture was extracted with EtOAc (2×5 mL) and the combined organic phases were dried (Na2SO4), filtered, concentrated and purified by preparative HPLC to give 12-(4-chloro-benzenesulfonyl)-4,5,12-triaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene-10-carboxylic acid as a white solid. Retention time (min)=1.316, method [1], MS (ESI) 382.0 (M+H); 1H NMR (300 MHz, CDCl3) δ 7.56 (d, J=8.7 Hz, 2H), 7.30-7.22 (m, 3H), 5.30-5.25 (m, 1H), 4.54-4.45 (m, 1H), 2.80 (dd, J=17.0, J=7.7 Hz, 1H), 2.50 (d, J=17.0 Hz, 1H), 2.42-2.30 (m, 1H), 2.24-1.85 (m, 4H).

Workup

  1. extractionThe reaction mixture was extracted with EtOAc (2×5 mL)
  2. dry with materialthe combined organic phases were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-e8ac724cd72a4d6ab28543597cb48cc1
Source dataset
uspto-grants-2010_07
Patent number
US07754712B2

Reaction notes

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