Hydrochloric Acid → HCID 46207711, compound

HRID 2209344Notes

Reaction equation

HRID 2209344 reaction equation
[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]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 46207474HCID 46207474, compound

Product 1

HCID 46207711HCID 46207711, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-a86b861f701b482683fc4264b7e97de7
Source dataset
uspto-grants-2016_06
Patent number
US09376383B2

Reaction notes

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