Triethylamine → HCID 70284605, compound

HRID 1637169Notes

Reaction equation

HRID 1637169 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([NH:15][CH2:16][C:17]([OH:19])=[O:18])=[O:14])([CH3:11])([CH3:10])[CH3:9].ClC(OCC)=O.[CH3:26][O:27][C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH2:30][NH2:31]>ClCCl>[C:8]([O:12][C:13]([NH:15][CH2:16][C:17]([OH:19])=[O:18])=[O:14])([CH3:11])([CH3:9])[CH3:10].[CH3:26][O:27][C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH2:30][NH2:31]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 812922-Methoxybenzylamine

Product 1

HCID 70284605HCID 70284605, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

6.6 g triethylamine were added to 10.0 g N-(tert.butoxycarbonyl)glycine in 100 ml dichloromethane. Then 6.2 g ethyl chloroformate in 20 ml dichloromethane were added dropwise at 0° C.; the mixture was stirred for 15 minutes at 0° C., and then a solution of 8.1 g 2-methoxybenzylamine in 25 ml dichloromethane was added thereto dropwise. The mixture was stirred for another 3 hours at room temperature before being extracted once with 100 ml of a 10% aqueous tartaric acid solution. The organic phase was dried over magnesium sulfate, filtered and reduced in volume under a vacuum. 13.9 g N-(tert.butoxycarbonyl)-glycine-(2-methoxybenzyl)amine were obtained, having a melting point of 96-97° C.

Workup

  1. stirringThe mixture was stirred for another 3 hours at room temperature
  2. extractionbefore being extracted once with 100 ml of a 10% aqueous tartaric acid solution
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-d9c9d2457b8f4e699ad9cd7bc9db8775
Source dataset
uspto-grants-2000_03
Patent number
US06040303

Reaction notes

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