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

HRID 534234ノート

反応式

HRID 534234 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-964b240f7a034457b759cc6978c00319
出典データセット
uspto-grants-2014_10
特許番号
US08853408B2

反応ノート

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