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

HRID 529382ノート

反応式

HRID 529382 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-626565d0282d48e4809d7186680aa899
出典データセット
uspto-grants-2016_05
特許番号
US09346840B2

反応ノート

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