Sodium Hydroxide → Nalpha-[3-(2-Hydroxyphenyl)acryloyl]-1-Methyl-L-Tryptophan

HRID 1746547Notes

Reaction equation

HRID 1746547 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]=[CH:12][C:13]([NH:15][C@H:16]([C:28]([O:30]C)=[O:29])[CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([CH3:27])[CH:19]=1)=[O:14])(=O)C.[OH-].[Na+]>CO>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]=[CH:12][C:13]([NH:15][C@H:16]([C:28]([OH:30])=[O:29])[CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]([CH3:27])[CH:19]=1)=[O:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86655453Methyl Nalpha-[3-(2-Acetoxyphenyl)acryloyl]-1-Methyl-L-Tryptophanate

Product 1

HCID 86655495Nalpha-[3-(2-Hydroxyphenyl)acryloyl]-1-Methyl-L-TryptophanYield 62.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The same procedures as in Example 64 were carried out from the compound obtained in Example 21 (3.9 g), 1 mol/L of an aqueous sodium hydroxide solution (28 mL), and methanol (140 mL), to give the captioned compound (2.1 g, 62%) as crystals.

Sources & evidence

ORD record
ord-cb86c26c78a4416b95dc1fbb74257e5e
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

Loading…