Sodium Hydroxide → 4-(3-(2-((((1R,2S)-2-Phenylcyclopropyl)amino)methyl)morpholino)propyl)benzoic acid

HRID 534234Notes

Reaction equation

HRID 534234 reaction equation
FC(F)(F)C([N:5]([CH2:15][CH:16]1[CH2:21][N:20]([CH2:22][CH2:23][CH2:24][C:25]2[CH:35]=[CH:34][C:28]([C:29]([O:31]CC)=[O:30])=[CH:27][CH:26]=2)[CH2:19][CH2:18][O:17]1)[C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[OH-].[Na+]>CO>[C:9]1([C@@H:7]2[CH2:8][C@H:6]2[NH:5][CH2:15][CH:16]2[CH2:21][N:20]([CH2:22][CH2:23][CH2:24][C:25]3[CH:35]=[CH:34][C:28]([C:29]([OH:31])=[O:30])=[CH:27][CH:26]=3)[CH2:19][CH2:18][O:17]2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86708275Ethyl 4-(3-(2-((2,2,2-trifluoro-N-((1R,2S)-2-phenylcyclopropyl)acetamido)methyl)morpholino)propyl)benzoate

Product 1

HCID 665715914-(3-(2-((((1R,2S)-2-Phenylcyclopropyl)amino)methyl)morpholino)propyl)benzoic acidYield 76.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-(3-(2-((2,2,2-trifluoro-N-((1R,2S)-2-phenylcyclopropyl)acetamido)methyl)morpholino)propyl)benzoate (190 mg, 0.366 mmol) in methanol (3 mL) was added sodium hydroxide (6M, 0.5 mL, 3.00 mmol), and the mixture was stirred at room temperature for 18 h. The mixture was purified using reverse-phase HPLC. The fractions containing the product were combined, treated with 1N HCl and concentrated. The residue was dried under vacuum to give 110 mg of product (HCl salt) as white solid. MS: (M+H)+=395.2. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.21-1.35 (m, 1H), 1.47-1.61 (m, 1H), 2.00-2.17 (m, 2H), 2.65-3.22 (m, 9H), 3.25-3.51 (m, 3H), 3.60 (br. s., 1H), 3.88-4.15 (m, 2H), 4.38 (br. s., 1H), 7.14-7.26 (m, 3H), 7.27-7.34 (m, 2H), 7.38 (d, J=8.08 Hz, 2H), 7.90 (d, J=8.08 Hz, 2H).

Workup

  1. customThe mixture was purified
  2. additionThe fractions containing the product
  3. additiontreated with 1N HCl
  4. concentrationconcentrated
  5. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-964b240f7a034457b759cc6978c00319
Source dataset
uspto-grants-2014_10
Patent number
US08853408B2

Reaction notes

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