Triethylamine → 3-Hydroxy-4-[(2-tert.-butoxycarbonylaminoacetyl)amino]-benzoic acid

HRID 1089672Notes

Reaction equation

HRID 1089672 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].C(N(CC)CC)C.[C:19]([O:23][C:24]([NH:26][CH2:27][C:28](O)=[O:29])=[O:25])([CH3:22])([CH3:21])[CH3:20]>CN(C)C=O>[OH:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[NH:1][C:28](=[O:29])[CH2:27][NH:26][C:24]([O:23][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:25])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 1375664-Amino-3-hydroxybenzoic acid

Product 1

HCID 156110193-Hydroxy-4-[(2-tert.-butoxycarbonylaminoacetyl)amino]-benzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 9.75 g of 4-amino-3-hydroxybenzoic acid and 9.75 ml of triethylamine in 90 ml of dimethylformamide is heated to 80° C. 20 g of the N-hydroxysuccinimide ester of N-tert.-butoxycarbonylglycine are added and the reaction mixture is kept at 80° C for 4 hours.

Sources & evidence

ORD record
ord-312172802cd448cbb74808e82ce853ee
Source dataset
uspto-grants-1992_01
Patent number
US05079241

Reaction notes

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