Sodium Hydroxide → HCID 10480044, compound

HRID 1353475Notes

Reaction equation

HRID 1353475 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([NH:20][C@H:21]3[CH2:27][CH2:26][CH2:25][CH2:24][N:23]([CH2:28][C:29]([O:31]C)=[O:30])[C:22]3=[O:33])=[O:19])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:34])=[CH:7][CH:8]=2)[N:3]=1.[OH-].[Na+]>C1COCC1>[NH2:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:13][CH2:14][N:15]([C:18]([NH:20][C@H:21]3[CH2:27][CH2:26][CH2:25][CH2:24][N:23]([CH2:28][C:29]([OH:31])=[O:30])[C:22]3=[O:33])=[O:19])[CH2:16][CH2:17]2)[C:9]2[C:4](=[CH:5][C:6]([Cl:34])=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10390804HCID 10390804, compound

Product 1

HCID 10480044HCID 10480044, compoundYield 5.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (3S)-[[[4-(2-amino-7-chloro-4-quinolinyl)-1-piperazinyl]carbonyl]amino]hexahydro-2-oxo-1H-azepine-1-acetic acid, methyl ester (300 mg, 0.613 mmol) in THF (3.0 mL) was added 2N NaOH solution (3 mL) at rt. After 30 min, THF was evaporated in vacuo, and the resulting residue was acidified to pH 4–5. The reaction mixture was extracted with ethyl acetate, washed with brine, and dried over Na2SO4. The product (15 mg) was obtained after concentration in vacuo. LC-MS: 475 (M++1). 1H NMR (CD3OD) δ 7.82 (d, 1H), 7.50 (s, 1H), 7.38 (d, 1H), 6.25 (s, 1H), 4.58 (d, 1H), 4.10 (m, 2H), 3.80 (m, 1H), 3.65 (m, 4H), 3.30 (m, 5H), 1.60–1.96 (m, 6H).

Workup

  1. customTHF was evaporated in vacuo
  2. extractionThe reaction mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-9df46fc4b2d2407eb77d04f882e1142d
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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