Hydrochloric Acid → HCID 60104851, compound

HRID 1612096Notes

Reaction equation

HRID 1612096 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[C@H:5]([CH2:20][S:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[NH:6][C:7](=[O:19])[C:8]([NH:11][C:12]([O:14]C(C)(C)C)=O)([CH3:10])[CH3:9])[CH3:2].[OH-].[Na+].Cl>CCO>[CH2:1]([O:3][C:4](=[O:29])[C@H:5]([CH2:20][S:21][CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[NH:6][C:7](=[O:19])[C:8]([NH:11][C:12](=[O:14])[C@@H:22]([SH:21])[CH:23]([CH3:28])[CH3:24])([CH3:9])[CH3:10])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23519196HCID 23519196, compound

Product 1

HCID 60104851HCID 60104851, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under an argon atmosphere, the thioacetyl compound of Example 2 (0.48 g, 1.0 mmol) is dissolved in absolute EtOH (5 mL) and treated with 1 N NaOH of (1.0 mL, 1.0 mmol). The mixture is stirred for 4 hours at room temperature before treatment with 1 N HCl until pH 3. The mixture is evaporated to remove most of the EtOH and the aqueous residue is extracted with EtOAc (2×10 mL). The combined extracts are washed with H2O (5 mL) and then with brine solution (5 mL). The solution is dried over Na2SO4, filtered and concentrated in vacuo. The product solidifies from tert-butyl methyl ether/hexane to give product; m.p. 87–91° C.

Workup

  1. customThe mixture is evaporated
  2. customto remove most of the EtOH
  3. extractionthe aqueous residue is extracted with EtOAc (2×10 mL)
  4. washThe combined extracts are washed with H2O (5 mL)
  5. dry with materialThe solution is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give product

Sources & evidence

ORD record
ord-2a2ee266fa714123a495a2aaf4389239
Source dataset
uspto-grants-2006_01
Patent number
US06992105B2

Reaction notes

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