Sodium Hydroxide → HCID 10061384, compound

HRID 2233535Notes

Reaction equation

HRID 2233535 reaction equation
[OH:1][CH2:2][CH:3]([NH:8][C:9]([C:11]1[CH:20]=[CH:19][C:14]2[NH:15][C:16](=[O:18])[NH:17][C:13]=2[CH:12]=1)=[O:10])[C:4]([O:6]C)=[O:5].[OH-].[Na+]>CO>[OH:1][CH2:2][CH:3]([NH:8][C:9]([C:11]1[CH:20]=[CH:19][C:14]2[NH:15][C:16](=[O:18])[NH:17][C:13]=2[CH:12]=1)=[O:10])[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 9970824HCID 9970824, compound

Product 1

HCID 10061384HCID 10061384, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The methyl ester adduct benzimidazol-2-one-5-carboxy-(L-serine)-amide (9) (100 mg, 0.3584 mmol) was suspended in methanol (10 mL) and on addition of 1M aq NaOH (0.68 mL, 0.680 mmol) readily dissolved. The disappearance of starting material was monitored with TLC and complete after stirring overnight at room temperature. The volume was increased by addition of further methanol (30 mL) and the pH carefully adjusted from 10 to 5 by the addition of Dowex 50 W-X8(H+) resin. The resin was rapidly filtered off and washed with further methanol (4×20 mL) and the combined filtrates rotary evaporated to dryness to give benzimidazol-2-one-5-carboxy-(L-serine)-amide (10) (91 mg, 96% yield) as a white powder;

Workup

  1. dissolutionreadily dissolved
  2. additionthe pH carefully adjusted from 10 to 5 by the addition of Dowex 50 W-X8(H+) resin
  3. filtrationThe resin was rapidly filtered off
  4. washwashed with further methanol (4×20 mL)
  5. customthe combined filtrates rotary evaporated to dryness

Sources & evidence

ORD record
ord-a007e82b29b54c2d893400cebe66e3a2
Source dataset
uspto-grants-2010_05
Patent number
US07709514B2

Reaction notes

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