1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Methyl 5-(2-(tert-butoxycarbonylamino)acetamido)-2-hydroxybenzoate

HRID 1525979Notes

Reaction equation

HRID 1525979 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:13]([NH:20][CH2:21][C:22](O)=[O:23])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].CCN=C=NCCCN(C)C.CN(C1C=CC=CN=1)C>ClCCl>[C:16]([O:15][C:13]([NH:20][CH2:21][C:22]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])=[O:23])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 135127Methyl 5-amino-2-hydroxybenzoate

Product 1

HCID 67174569Methyl 5-(2-(tert-butoxycarbonylamino)acetamido)-2-hydroxybenzoateYield 46.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 5-amino-2-hydroxybenzoate (1.5 g, 9.0 mmol) in dichloromethane (50 mL) was added BOC-glycine (1.57 g, 9.0 mmol), EDCI (1.89 g, 9.9 mmol) and dimethylaminopyridine (0.11 g, 0.9 mmol). The reaction was stirred (RT, 2.5 h), and then partitioned between CH2Cl2 and brine. The aqueous layer was extracted with CH2Cl2 and the combined organic layers were washed with brine and dried over MgSO4. The crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to afford methyl 5-(2-(tert-butoxycarbonylamino)-acetamido)-2-hydroxybenzoate (1.37 g). Mass calculated for C15H20N2O6=324.33; found: [M+Na]+=347.2.

Workup

  1. custompartitioned between CH2Cl2 and brine
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. customThe crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-16339744c4bd4266b73b8f6f91082d78
Source dataset
uspto-grants-2015_07
Patent number
US09085527B2

Reaction notes

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