Methanol → N-([1,1'-Biphenyl]-4-carbonyl)-D-glutamic acid

HRID 1672247Notes

Reaction equation

HRID 1672247 reaction equation
C([O:3][C:4](=[O:28])[CH:5]([NH:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:18][CH:17]=1)=[O:15])[CH2:6][CH2:7][C:8]([O:10]CC)=[O:9])C.CO.[OH-].[Na+]>C1COCC1>[C:19]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:18]=[CH:17][C:16]([C:14]([NH:13][C@@H:5]([C:4]([OH:28])=[O:3])[CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[O:15])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67334930HCID 67334930, compound

Product 1

HCID 15984771N-([1,1'-Biphenyl]-4-carbonyl)-D-glutamic acidYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[(Biphenyl-4-carbonyl)-amino]-pentanedioic acid diethyl ester (250 mg, 0.65 mmol) in THF (6 mL) was added to MeOH (6 mL), followed by the addition of 1N NaOH solution (5.2 mL, 5.2 mmol, 8 eq.). The mixture was stirred at room temperature overnight. Reaction was complete as determined by HPLC. Solvents were removed by rotavap and a small amount of water (5 mL) was added to make a homogeneous solution. 1N HCl was added dropwise until the solution reached a pH of 4. The solid precipitate was collected by filtration, washed with EtOAc, and dried in vacuum oven. Product N-(1,1′-biphenyl-4-ylcarbonyl)-D-glutamic acid (189 mg) was isolated in 89% yield. MS (ESI) m/z 326.

Workup

  1. customReaction
  2. customSolvents were removed by rotavap
  3. additiona small amount of water (5 mL) was added
  4. addition1N HCl was added dropwise until the solution
  5. filtrationThe solid precipitate was collected by filtration
  6. washwashed with EtOAc
  7. customdried in vacuum oven

Sources & evidence

ORD record
ord-7396d7e1cd574956959264e9a37f6dfb
Source dataset
uspto-grants-2011_08
Patent number
US07998965B2

Reaction notes

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