Sodium Hydroxide → Sodium 2-{[3-{[(3-amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl) (cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenoxy]methyl}cyclopropanecarboxylate

HRID 561880Notes

Reaction equation

HRID 561880 reaction equation
[NH2:1][CH2:2][CH:3]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][O:42][C:43]2[C:48]([Cl:49])=[CH:47][C:46]([CH3:50])=[CH:45][C:44]=2[Cl:51])=[CH:35][CH:34]=1)[C:4]([N:6]([CH2:10][C:11]1[CH:12]=[C:13]([CH:24]=[C:25]([CH2:27][CH2:28][CH2:29][O:30][CH3:31])[CH:26]=1)[O:14][CH2:15][CH:16]1[CH2:18][CH:17]1[C:19]([O:21]CC)=[O:20])[CH:7]1[CH2:9][CH2:8]1)=[O:5].[OH-].[Na+:53]>C(O)C>[NH2:1][CH2:2][CH:3]([CH2:32][C:33]1[CH:34]=[CH:35][C:36]([O:39][CH2:40][CH2:41][O:42][C:43]2[C:44]([Cl:51])=[CH:45][C:46]([CH3:50])=[CH:47][C:48]=2[Cl:49])=[CH:37][CH:38]=1)[C:4]([N:6]([CH2:10][C:11]1[CH:12]=[C:13]([CH:24]=[C:25]([CH2:27][CH2:28][CH2:29][O:30][CH3:31])[CH:26]=1)[O:14][CH2:15][CH:16]1[CH2:18][CH:17]1[C:19]([O-:21])=[O:20])[CH:7]1[CH2:9][CH2:8]1)=[O:5].[Na+:53]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15981220HCID 15981220, compound

Product 1

HCID 23686336Sodium 2-{[3-{[(3-amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl) (cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenoxy]methyl}cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a ethanol solution (0.03 M) of ethyl 2-{[3-{[(3-amino-2-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]benzyl}propanoyl) (cyclopropyl)amino]methyl}-5-(3-methoxypropyl)phenoxy]methyl}cyclopropanecarboxylate from Example 86 was added sodium hydroxide (1 N aqueous solution, 2.2 eq.). The resulting solution was stirred at 80° C. for 18 h. The volatiles were removed in vacuo and the resulting solid residue was suspended in dichloromethane. The insolubles were then filtered off and the filtrate was concentrated in vacuo to afford the title compound as a white solid. MS for the corresponding free acid (ESI+): 713.2. 1H NMR (methanol-d4): 0.41 (m, 1H), 0.70-0.83 (m, 4H), 1.11 (m, 1H), 1.52 (m, 1H), 1.72 (m, 1H), 1.80-1.87 (m, 2H), 2.24 (m, 1H), 2.31 (s, 3H), 2.59-2.62 (m, 2H), 2.75-2.80 (m, 2H), 2.84 (dd, J=13.2, 9.5 Hz, 1H), 2.95 (dd, J=12.7, 7.5 Hz, 1H), 3.31 (s, 3H), 3.37 (t, J=6.4 Hz, 2H), 3.73 (71, 1H), 3.85 (d, J=6.7 Hz, 2H), 4.22-4.45 (m, 4H), 4.48 (d, J=14.6 Hz, 1H), 4.58 (d, J=14.8 Hz, 1H), 6.58 (s, 1H), 6.62 (s, 1H), 6.65 (s, 1H), 6.78 (d, J=8.6 Hz, 2H), 7.08 (d, J=8.5 Hz, 2H), 7.22 (s, 2H).

Workup

  1. customThe volatiles were removed in vacuo
  2. filtrationThe insolubles were then filtered off
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-15c7ede725a246189bede1979e45a7d3
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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