Water → HCID 10595001, compound

HRID 2292776Notes

Reaction equation

HRID 2292776 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:30])[CH2:6][CH2:7][NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]([CH3:25])=[C:12]2[CH2:26][C:27]([NH2:29])=[O:28].O>CO>[NH2:29][C:27](=[O:28])[CH2:26][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([NH:8][CH2:7][CH2:6][C:5]([OH:30])=[O:4])[CH:10]=2)[N:14]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]=1[CH3:25]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 10691130HCID 10691130, compound

Product 1

HCID 10595001HCID 10595001, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

One mL of 1N NaOH was added to a solution of 110 mg (0.3 mmol) of 3-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-5-yl]amino]propanoic acid methyl ester (Example 26) in 5 mL of MeOH, stirred 1.0 hour, then 1 mL of 1N NaOH was added and the mixture stirred 0.5 hour. Water was added, then 2 mL of 1N HCl, and the mixture extracted with EtOAc. This was dried (MgSO4) and concentrated at reduced pressure to give 21 mg (20% yield) of 3-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-5-yl]amino]propanoic acid.

Workup

  1. stirringthe mixture stirred 0.5 hour
  2. extraction2 mL of 1N HCl, and the mixture extracted with EtOAc
  3. dry with materialThis was dried (MgSO4)
  4. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-1dc002e065c74bf49b9f7483df357958
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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