Hydrochloric Acid → HCID 11613197, compound

HRID 551905Notes

Reaction equation

HRID 551905 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:39]=[CH:38][C:16]([CH2:17][N:18]([CH2:25][C:26]3[CH:37]=[CH:36][C:29]([O:30][CH2:31][C:32]([O:34]C)=[O:33])=[CH:28][CH:27]=3)[C:19]([NH:21][CH2:22][CH2:23][CH3:24])=[O:20])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl>CO.C1COCC1>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:39]=[CH:38][C:16]([CH2:17][N:18]([CH2:25][C:26]3[CH:37]=[CH:36][C:29]([O:30][CH2:31][C:32]([OH:34])=[O:33])=[CH:28][CH:27]=3)[C:19]([NH:21][CH2:22][CH2:23][CH3:24])=[O:20])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11562742HCID 11562742, compound

Product 1

HCID 11613197HCID 11613197, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of methyl [4-({{4-[(4-butylphenyl)ethynyl]benzyl}[(propylamino)carbonyl]-amino}methyl)phenoxy]acetate (47 mg, 0.089 mmol) in MeOH/THF (2 ml, (1/1)) was added an aqueous solution of NaOH (2 mL, 1N). The reaction mixture was stirred at rt for 2 hrs. Then an aqueous solution of HCl (7 mL, 1N) was added and extracted with Et2O (2×7 mL). The combined organic layers were dried over Na2SO4 and the solvents were removed under reduced pressure to give 42 mg (77%) of the title compound as a yellow oil. HPLC, Rt: 5.1 min (purity: 83.9%). LC/MS, M+(ESI): 513.4, M−(ESI): 511.4. 1H NMR (DMSO-d6) Ε: 7.49 (d, J=8.3 Hz, 2H), 7.44 (d, J=7.9 Hz, 2H), 7.22 (m, 4H), 7.11 (d, J=8.8 Hz, 2H), 6.86 (d, J=8.8 Hz, 2H), 6.53 (t, J=5.3 Hz, 1H), 4.63 (s, 2H), 4.37 (s, 2H), 4.31 (s, 2H), 3.03 (m, 2H), 2.60 (t, J=7.7 Hz, 2H), 1.58-1.22 (m, 6H), 0.89 (t, J=7.3 Hz, 3H), 0.78 (t, J=7.4 Hz, 3H).

Workup

  1. extractionextracted with Et2O (2×7 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-9d9e6bc9851b44b0b17138aa93c91790
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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