Hydrochloric Acid → HCID 46207711、化合物

HRID 2209344ノート

反応式

HRID 2209344 の反応式
[CH3:1]/[C:2](/[CH2:22][CH2:23]/[CH:24]=[C:25](\[CH3:32])/[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])=[CH:3]\[CH2:4][S:5][CH2:6][C@@H:7]([C:19]([OH:21])=[O:20])[NH:8][C:9](=[O:18])[NH:10][CH2:11][CH2:12][C:13](=[O:17])[O:14]CC.[Li+].[OH-].C(OCC)(=O)C.Cl>C1COCC1.O>[C:13]([CH2:12][CH2:11][NH:10][C:9](=[O:18])[NH:8][C@@H:7]([CH2:6][S:5][CH2:4]/[CH:3]=[C:2](\[CH3:1])/[CH2:22][CH2:23]/[CH:24]=[C:25](\[CH3:32])/[CH2:26][CH2:27][CH:28]=[C:29]([CH3:30])[CH3:31])[C:19]([OH:21])=[O:20])([OH:17])=[O:14]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 46207474HCID 46207474、化合物

生成物 1

HCID 46207711HCID 46207711、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

In a 100 mL round bottom flask, Compound D of Example 6 (100 mg, 0.21 mmol) was dissolved in THF (10 mL). LiOH (500 mg, 20 mmol) in water (5 mL) was added to the reaction solution. The reaction mixture was stirred at room temperature overnight. Ethyl acetate (100 mL) was added to the reaction mixture. The reaction mixture was acidified by 1 N HCl solution (pH=4.0). The organic portion was separated and dried over Na2SO4, concentrated and purified by HPLC (40 mg, 41%) to yield Compound G. 1H-NMR (500 MHz, MeOH-d4): δ 1.62 (bs, 6H), 1.69 (s, 3H), 1.70 (s, 3H), 1.99 (m, 2H), 2.08 (m, 6H), 2.51 (t, J=6.5, 2H), 2.79 (dd, J=7.0, 14.0 Hz, 1H), 2.93 (dd, J=4.5, 8.1 Hz, 1H), 3.17 (dd, J=7.0, 13.0 Hz, 1H), 3.28 (dd, J=9.0, 15.0 Hz, 1H), 3.40 (t, J=6.5 Hz, 3H), 4.50 (dd, J=5.0, 6.5 Hz, 1H), 5.11 (m, 2H), 5.23 (t, J=7.5, 1H). 13C-NMR (125 MHz, MeOH-d4): δ 16.1, 16.2, 17.8, 26.0, 27.4, 27.8, 30.5, 34.4, 35.7, 36.8, 40.8, 40.9, 54.1, 121.7, 125.2, 125.5, 132.1, 136.3, 140.5, 160.3, 175.1, 175.7; ES-MS: mass calcd for Chemical Formula: C22H36N2O5S 440.6. Found (M+Na) m/z 463.3.

後処理

  1. customThe organic portion was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by HPLC (40 mg, 41%)

出典と根拠

ORDレコード
ord-a86b861f701b482683fc4264b7e97de7
出典データセット
uspto-grants-2016_06
特許番号
US09376383B2

反応ノート

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