Methanol → HCID 58188052, compound

HRID 1845240Notes

Reaction equation

HRID 1845240 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[CH:11]=[C:10]([C:21]([O:23]CC)=[O:22])[CH:9]=2)=[CH:4][CH:3]=1.CO.[OH-].[Li+]>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([N:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)=[O:15])[CH:11]=[C:10]([C:21]([OH:23])=[O:22])[CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 58188319HCID 58188319, compound

Product 1

HCID 58188052HCID 58188052, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 4′-bromo-5-(pyrrolidine-1-carbonyl)biphenyl-3-carboxylate (3.3 g, 8.2 mmol), MeOH (100 mL), water (20 mL), and lithium hydroxide (0.90 g, 38 mmol) was stirred at room temperature for 3 h. The mixture was concentrated in vacuo and the residue was acidified with 1N aq. HCl to pH 2-3 and extracted with EtOAc (2×100 mL). The combined organic layers were dried (Na2SO4) and concentrated to afford a white foam. LC-MS: 376.1 [M+1]+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with EtOAc (2×100 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. customto afford a white foam

Sources & evidence

ORD record
ord-51233f3cdb82476d866d1ed9bd5fa954
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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