Methyl 5-(2-(tert-butoxycarbonylamino)acetamido)-2-hydroxybenzoate → Methyl 5-(2-aminoacetamido)-2-hydroxybenzoate

HRID 85388Notes

Reaction equation

HRID 85388 reaction equation
C(OC([NH:8][CH2:9][C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:11])=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:8][CH2:9][C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:11]

Participants

4

Reactant 1

HCID 67174569Methyl 5-(2-(tert-butoxycarbonylamino)acetamido)-2-hydroxybenzoate

Product 1

HCID 59193335Methyl 5-(2-aminoacetamido)-2-hydroxybenzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The methyl 5-(2-(tert-butoxycarbonylamino)-acetamido)-2-hydroxybenzoate (1.3 g, 4.0 mmol) was dissolved in CH2Cl2 (15 mL) and TFA (8 mL). The reaction was stirred (RT, 2.5 h) and then concentrated to afford methyl 5-(2-aminoacetamido)-2-hydroxybenzoate as a clear oil. Found [M+H]+=225.1. The oil was dissolved in CH2Cl2 (20 mL) and to this was added DHA (1.3 g, 4.0 mmol), EDCI (0.84 g, 4.4 mmol) and triethylamine (2.0 g, 20.0 mmol). The reaction was stirred (RT, 4 h) and then partitioned between CH2Cl2 and brine. The aqueous layer was extracted with CH2Cl2, and the combined organic layers were dried over MgSO4. The crude material was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to afford methyl 5-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoacetamido)-2-hydroxybenzoate (0.9 g) as a tan solid. Mass calculated for C10H12N2O4=534.69; found: [M+H]+=535.4.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-fd3c2768a87d456385c2bea75839bb99
Source dataset
uspto-grants-2014_09
Patent number
US08846972B2

Reaction notes

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