O-Methyltyramine → HCID 131716192, compound

HRID 1638351Notes

Reaction equation

HRID 1638351 reaction equation
[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:14]([OH:16])=[O:15])[CH2:3][C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1CCC(N=C=NC2CCCCC2)CC1.[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][NH2:49])=[CH:43][CH:42]=1>C(Cl)Cl>[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:14]([OH:16])=[O:15])[CH2:3][C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([CH2:47][CH2:48][NH-:49])=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 4657O-MethyltyramineHCID 10868DicyclohexylcarbodiimideHCID 1581888N-tert-Butoxycarbonyl-L-aspartic acid beta-benzyl ester

Product 1

HCID 131716192HCID 131716192, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boc-Asp(OBzl)-OH (38.8 g; 0.12 Mole) was dissolved in CH2Cl2 (250 ml) and cooled in a dry ice/acetone bath. DCC (24.75 g; 0.12 Mole) dissolved in CH2Cl2 (50 ml) was added slowly. After stirring for 10 minutes 4-methoxyphenylethyl amine (15.1 g; 0.1 Mole) was added dropwise and stirring was continued for another hour at room temperature. The mixture was filtered and the filtrate was washed with saturated NaHCO3 solution (×50 ml) and 1N HCl (50 ml). The organic phase was dried over sodium sulfate and evaporated to an oil. Yield: 41.5 g; FAB-MS: (M+Li)=463.

Workup

  1. temperaturecooled in a dry ice/acetone bath
  2. additionwas added slowly
  3. additionwas added dropwise
  4. waitwas continued for another hour at room temperature
  5. filtrationThe mixture was filtered
  6. washthe filtrate was washed with saturated NaHCO3 solution (×50 ml) and 1N HCl (50 ml)
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. customevaporated to an oil

Sources & evidence

ORD record
ord-bfbab411f5a44c108a8ac0954937deaa
Source dataset
uspto-grants-1989_11
Patent number
US04879313

Reaction notes

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