Hydrochloric Acid → HCID 66920731, compound

HRID 1364557Notes

Reaction equation

HRID 1364557 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:15][CH2:16][C:17]2[CH:29]=[CH:28][C:20]([O:21][CH2:22][C:23]([O:25]CC)=[O:24])=[CH:19][CH:18]=2)=[O:14])[CH:3]=1.CO.[OH-].[Na+].Cl>O1CCCC1>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH2:11][CH3:12])[N:5]=[C:4]([C:13]([NH:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:28][CH:29]=2)=[O:14])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 90893276HCID 90893276, compound

Product 1

HCID 66920731HCID 66920731, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 188A (102 mg, 0.26 mmol) in a mixed solvent of methanol (2 mL) and tetrahydrofuran (2 mL) was added 2N NaOH (300 μL, 0.6 mmol). The reaction mixture was stirred at ambient temperature for 2 hr, and then acidified with 600 μL 1N HCl. It was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo to provide the titled compound as white solid (95 mg, 100%).

Workup

  1. customIt was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4fbce52773214202bf2059efc3d7c51e
Source dataset
uspto-grants-2011_02
Patent number
US07888374B2

Reaction notes

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