Acetic Acid → HCID 56941311, compound

HRID 589714Notes

Reaction equation

HRID 589714 reaction equation
[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[S:16]([NH:19][C:20]1[CH:21]=[C:22]([CH:28]=[CH:29][CH:30]=1)[C:23]([O:25]CC)=[O:24])(=[O:18])=[O:17].[Li+].[OH-].C(O)(=O)C>C1COCC1.O>[CH3:1][C:2]1[C:6]2[CH:7]=[C:8]([N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[S:16]([NH:19][C:20]1[CH:21]=[C:22]([CH:28]=[CH:29][CH:30]=1)[C:23]([OH:25])=[O:24])(=[O:17])=[O:18]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3939Lithium HydroxideHCID 66800032HCID 66800032, compound

Product 1

HCID 56941311HCID 56941311, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

The ethyl 3-{[(3-methyl-5-pyrrolidin-1-yl-1-benzothiophen-2-yl)sulfonyl]amino}benzoate (4.7 mg, 0.01 mmol) was hydrolyzed with LiOH (2.6 mg, 0.06 mmol) in THF/water (1:1, 2 mL) at 55° C. over night. The reaction mixture was neutralized with acetic acid (3.6 μL) and the mixture was concentrated. The crude product was purified by preparative HPLC (ACE C8, 5 μm 21×50 mm, flow 25 ml/min, 50 mM NH4OAc in water/CH3CN) to give 2.7 mg (6% over two steps) of the title compound. MS (ESI+) calcd for C20H20N2O4S2 416.086449, found 416.086649.

Workup

  1. concentrationthe mixture was concentrated
  2. customThe crude product was purified by preparative HPLC (ACE C8, 5 μm 21×50 mm, flow 25 ml/min, 50 mM NH4OAc in water/CH3CN)

Sources & evidence

ORD record
ord-59034a46c8804ebf801519ea1cc932d2
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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