Lithium hydroxide, monohydrate → HCID 178487507, compound

HRID 2279413Notes

Reaction equation

HRID 2279413 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[C:9]([O:20][CH2:21][CH2:22][C@H:23]2[CH2:28][CH2:27][C@H:26]([NH:29][C:30]([C:32]3[CH:33]=[CH:34][C:35]4[S:40][CH2:39][C:38](=[O:41])[NH:37][C:36]=4[CH:42]=3)=[O:31])[CH2:25][CH2:24]2)=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([O:18][CH3:19])[CH:12]=2)=[O:7]>O1CCCC1.O>[CH3:19][O:18][C:13]1[CH:12]=[C:11]2[C:16]([CH:17]=[C:8]([C:6]([OH:7])=[O:5])[C:9]([O:20][CH2:21][CH2:22][C@H:23]3[CH2:28][CH2:27][C@H:26]([NH:29][C:30]([C:32]4[CH:33]=[CH:34][C:35]5[S:40][CH2:39][C:38](=[O:41])[NH:37][C:36]=5[CH:42]=4)=[O:31])[CH2:25][CH2:24]3)=[N:10]2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178496936HCID 178496936, compound

Product 1

HCID 178487507HCID 178487507, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide monohydrate (18 mg, 0.42 mmol, 1.5 eq) is added at room temperature to a stirred solution of 7-methoxy-2-(2-{trans-4-[(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carbonyl)-amino]-cyclohexyl}-ethoxy)-quinoline-3-carboxylic acid methyl ester (173 mg, 0.28 mmol, 1.0 eq) in a mixture of tetrahydrofuran/water (6 mL, 2:1, v/v). After stirring at room temperature for 15 hours, solvents are evaporated and the residue is acidified to pH 5 with 0.5N hydrochloric acid aqueous solution and the resulting aqueous layer is extracted with dichloromethane (3×10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by preparative HPLC to afford 7-methoxy-2-(2-{trans-4-[(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carbonyl)-amino]-cyclohexyl}-ethoxy)-quinoline-3-carboxylic acid as an off-white lyophilizated powder (11 mg, 6% yield).

Workup

  1. customsolvents are evaporated
  2. extractionthe resulting aqueous layer is extracted with dichloromethane (3×10 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue that
  7. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-3c32773f9aff4440b45f11ec174f5bea
Source dataset
uspto-grants-2015_09
Patent number
US09133219B2

Reaction notes

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