1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(4-Benzyloxy-benzoylamino)-2-methyl-propionic acid methyl ester

HRID 1178000Notes

Reaction equation

HRID 1178000 reaction equation
CCN(C(C)C)C(C)C.[CH2:10]([O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:48][O:49][C:50](=[O:55])[C:51]([NH2:54])([CH3:53])[CH3:52]>CN(C=O)C.O>[CH3:48][O:49][C:50](=[O:55])[C:51]([NH:54][C:22](=[O:24])[C:21]1[CH:20]=[CH:19][C:18]([O:17][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:26][CH:25]=1)([CH3:53])[CH3:52]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 738804-(Benzyloxy)benzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 4186341Methyl 2-amino-2-methylpropanoate

Product 1

HCID 578556732-(4-Benzyloxy-benzoylamino)-2-methyl-propionic acid methyl esterYield 70.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (407 mg, 0.28 mL, 3.15 mmol) was added to a stirred solution of 4-benzyloxy-benzoic acid (200 mg, 0.87 mmol)(prepared by the method as described above) in DMF (2 mL). HOBT (142 mg, 1.05 mmol) and EDCI (201 mg, 1.05 mmol) were then added at room temperature. After 2 minutes, 2-amino-2-methyl-propionic acid methyl ester (161 mg, 1.05 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitated out to afford 200 mg (70% yield) of 2-(4-benzyloxy-benzoylamino)-2-methyl-propionic acid methyl ester. LCMS Purity: 93%.

Workup

  1. customprepared by the method
  2. filtrationfiltered the solid
  3. customprecipitated out

Sources & evidence

ORD record
ord-483bab042bdf407b9e99151034065882
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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