Lithium hydroxide, monohydrate → HCID 46206859, compound

HRID 1644728Notes

Reaction equation

HRID 1644728 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[C:30]([F:33])[CH:31]=4)[CH:26]=[C:25]([CH2:34][C:35]([O:37]CC)=[O:36])[CH:24]=3)=[O:22])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].O.[OH-].[Li+]>O1CCCC1.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[C:30]([F:33])[CH:31]=4)[CH:26]=[C:25]([CH2:34][C:35]([OH:37])=[O:36])[CH:24]=3)=[O:22])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59350824HCID 59350824, compound

Product 1

HCID 46206859HCID 46206859, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-[4-(3-ethoxycarbonylmethyl-7-fluoro-naphthalene-1-carbonyl)-benzenesulfonyl]-piperazine-1-carboxylic acid ethyl ester (0.110 g, 0.20 mmol) in tetrahydrofuran (12 mL) was added a solution of lithium hydroxide monohydrate (0.042 g, 0.99 mmol) in water (3 mL) and the reaction mixture was stirred for 14 hours at room temperature. The reaction mixture was concentrated under reduced pressure, diluted with water (6 mL) and washed with ethyl acetate (2×5 mL). The aqueous layer was acidified with an aqueous solution of hydrochloric acid (1 N), then extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 0.058 (56%) of 4-[4-(3-carboxymethyl-7-fluoro-naphthalene-1-carbonyl)-benzenesulfonyl]-piperazine-1-carboxylic acid ethyl ester as yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.51 (br. s, 1 H), 8.10-8.20 (m, 2H), 8.00 (d, J=8.3 Hz, 2 H), 7.90 (d, J=8.3 Hz, 2 H), 7.82-7.88 (m, 1 H), 7.72 (s, 1 H), 7.57 (td, J=8.7, 2.2 Hz, 1 H), 3.99 (q, J=6.9 Hz, 2 H), 3.82 (s, 2 H), 3.46 (br. s, 4 H), 2.96 (br. s, 4 H), 1.13 (t, J=6.9 Hz, 3 H). MS cald. for C26H25FN2O7S ([M+H]+) 529, obsd. 529.3.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water (6 mL)
  3. washwashed with ethyl acetate (2×5 mL)
  4. extractionextracted with ethyl acetate (3×10 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d5917598a02e44a998a877c61fdb0162
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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