Hydrochloric Acid → 4-({2-[(3,5-Bis-trifluoromethyl-benzyl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amino]-pyrimidine-5-carbonyl}-amino)-butyric acid

HRID 604124Notes

Reaction equation

HRID 604124 reaction equation
[F:1][C:2]([F:55])([F:54])[C:3]1[CH:4]=[C:5]([CH:47]=[C:48]([C:50]([F:53])([F:52])[F:51])[CH:49]=1)[CH2:6][N:7]([CH2:25][C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:27]=1[C:36]1[CH:41]=[C:40]([CH:42]([CH3:44])[CH3:43])[CH:39]=[CH:38][C:37]=1[O:45][CH3:46])[C:8]1[N:13]=[CH:12][C:11]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])=[O:15])=[CH:10][N:9]=1.[OH-].[Na+].Cl>C(O)C>[F:55][C:2]([F:1])([F:54])[C:3]1[CH:4]=[C:5]([CH:47]=[C:48]([C:50]([F:51])([F:52])[F:53])[CH:49]=1)[CH2:6][N:7]([CH2:25][C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:27]=1[C:36]1[CH:41]=[C:40]([CH:42]([CH3:44])[CH3:43])[CH:39]=[CH:38][C:37]=1[O:45][CH3:46])[C:8]1[N:9]=[CH:10][C:11]([C:14]([NH:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[O:15])=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86626871Ethyl 4-({2-[(3,5-bis-trifluoromethyl-benzyl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amino]-pyrimidine-5-carbonyl}-amino)-butyrate

Product 1

HCID 236418544-({2-[(3,5-Bis-trifluoromethyl-benzyl)-(5'-isopropyl-2'-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amino]-pyrimidine-5-carbonyl}-amino)-butyric acidYield 99.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-({2-[(3,5-bis-trifluoromethyl-benzyl)-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amino]-pyrimidine-5-carbonyl}-amino)-butyrate (230 mg) is dissolved in ethanol (5 ml) and thereto is added a 2M-aqueous sodium hydroxide solution (1 ml) and the mixture is stirred at room temperature for 1 hour and a half. To reaction mixture is added a 2N-hydrochloric acid and the mixture is extracted with ethyl acetate. 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=25:1) to give 4-({2-[(3,5-bis-trifluoromethyl-benzyl)-(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-amino]-pyrimidine-5-carbonyl}-amino)-butyric acid (220 mg). MS (m/z): 757 [M+H]+

Workup

  1. customTo reaction mixture
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (chloroform:methanol=25:1)

Sources & evidence

ORD record
ord-682754569d1e48818a4e2a8de8bed5ab
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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