Sodium Hydroxide → HCID 59745537, compound

HRID 2080543Notes

Reaction equation

HRID 2080543 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[CH:10]=[C:11]([C:24]([O:26]CC)=[O:25])[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:6]=2[CH2:5]1)(=[O:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[CH:10]=[C:11]([C:24]([OH:26])=[O:25])[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59745551HCID 59745551, compound

Product 1

HCID 59745537HCID 59745537, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 6-acetyl-1-[(4-methoxyphenyl)sulfonyl]-4,5,6,7-tetrahydro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate obtained in Example 2 under step c) (500 mg, 1.23 mmol) in ethanol (22.5 mL) at room temperature was added sodium hydroxide solution (590 mg, 14.76 mmol, 12 eq., in 22.5 mL H2O). The reaction mixture was stirred at rt for 48 hours and partitioned between 1 N HCl and EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. Purification by preparative HPLC followed by lyophilisation gave the title compound (183 mg, 39%).

Workup

  1. custompartitioned between 1 N HCl and EtOAc
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-1a2f5b841184472893921912002eb7e3
Source dataset
uspto-grants-2011_04
Patent number
US07932389B2

Reaction notes

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