Sodium Hydroxide → HCID 87263206, compound

HRID 604035Notes

Reaction equation

HRID 604035 reaction equation
C([O:4][CH2:5][CH2:6][N:7]([C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=1[CH2:27][N:28]([CH2:41][C:42]1[CH:47]=[C:46]([C:48]([F:51])([F:50])[F:49])[CH:45]=[C:44]([C:52]([F:55])([F:54])[F:53])[CH:43]=1)[C:29]1[N:34]=[CH:33][C:32]([N:35]2[CH2:40][CH2:39][O:38][CH2:37][CH2:36]2)=[CH:31][N:30]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])(=O)C.[OH-].[Na+:57]>C(O)C>[Na+:57].[F:51][C:48]([F:49])([F:50])[C:46]1[CH:47]=[C:42]([CH:43]=[C:44]([C:52]([F:53])([F:55])[F:54])[CH:45]=1)[CH2:41][N:28]([CH2:27][C:18]1[CH:19]=[C:20]([C:23]([F:24])([F:25])[F:26])[CH:21]=[CH:22][C:17]=1[N:7]([CH2:6][CH2:5][OH:4])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O-:16])=[O:15])[C:29]1[N:34]=[CH:33][C:32]([N:35]2[CH2:36][CH2:37][O:38][CH2:39][CH2:40]2)=[CH:31][N:30]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 87332946HCID 87332946, compound

Product 1

HCID 87263206HCID 87263206, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 7-[(2-acetoxy-ethyl)-(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-1-amino]-heptanoate (156 mg) is dissolved in ethanol (4 ml), and thereto is added 1N-aqueous sodium hydroxide solution (1 ml), and the mixture is stirred at room temperature for 4 hours. To the reaction solution are added 1N-hydrochloric acid and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (chloroform:methanol=1:0→19:1) to give 7-[(2-acetoxy-ethyl)-(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-amino]-heptanoic acid (144 mg). The resulting 7-[(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-(2-hydroxy-ethyl)-amino]-heptanoic acid (144 mg) is dissolved in ethanol (1 ml), and thereto is added a 1N-aqueous sodium hydroxide solution (172 μl), and concentrated under reduced pressure to give 7-[(2-{[(3,5-bis-trifluoromethyl-benzyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-(2-hydroxy-ethyl)-amino]-heptanoic acid sodium salt (133 mg). MS (m/z): 750 [M−Na]−

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b7d7741d8a284dec86cf6d6a9713b73f
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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