HCID 131724270, compound → HCID 131724269, compound

HRID 433849Notes

Reaction equation

HRID 433849 reaction equation
C[NH:2][C:3](=[O:22])[CH:4]([C:17](=[O:21])[CH2:18][NH:19][CH3:20])[CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1>CO.[OH-].[Na+].CO.O.[H][H]>[CH3:20][NH:19][CH2:18][C:17]([CH:4]([CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)[C:3]([NH2:2])=[O:22])=[O:21]

Participants

6

Reactant 1

HCID 131724270HCID 131724270, compound

Product 1

HCID 131724269HCID 131724269, compoundYield 90%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolventHCID 22242641Methanol--water (1/1)SolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

N-Methylglycylbiotinamide methyl ester was hydrolyzed in a mixture of 31 mL MeOH and 10 mL of 1N NaOH at room temperature with stirring for 1 hour. The mixture was diluted with 50 mL 50% MeOH/water and neutralized with cation exchange resin, hydrogen form (AG MP-50, BioRad). The solution was filtered, the resin washed (3×50 mL) with 50% MeOH/water, and the solvents removed by rotary evaporation to yield 1.6 g (90%) of N-methylglycylbiotinamide acid as an off-white solid. 1H-NMR. (Ref. Wilbur, D. S., Bioconj. Chem., v8 pp572-584)

Workup

  1. customform (AG MP-50, BioRad)
  2. filtrationThe solution was filtered
  3. washthe resin washed (3×50 mL) with 50% MeOH/water
  4. customthe solvents removed by rotary evaporation

Sources & evidence

ORD record
ord-f94fe99e94884af2b7bea45331ab3bf5
Source dataset
uspto-grants-2003_12
Patent number
US06670194B1

Reaction notes

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