Triethylamine → HCID 54445543, compound

HRID 1583245Notes

Reaction equation

HRID 1583245 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[NH:6][C:7](=[O:10])[CH2:8][NH2:9])[CH3:2].Br.[C:21]([O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=1)(=[O:23])[CH3:22].C(N(CC)CC)C.C(N=C=NCCCN(C)C)C.Cl>ClCCl>[CH2:1]([O:3][C:4](=[O:19])[C@H:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[NH:6][C:7](=[O:10])[CH2:8][NH:9][C:29](=[O:30])[C:28]1[CH:27]=[CH:26][C:25]([O:24][C:21](=[O:23])[CH3:22])=[CH:33][CH:32]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 16865Benzoic acid, 4-(acetyloxy)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86740489HCID 86740489, compound

Product 1

HCID 54445543HCID 54445543, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

17.4 g (0.05 mol) of glycyl-L-tyrosine ethyl ester·HBr, 9 g (0.05 mol) of p-acetoxybenzoic acid and 5.1 g (0.05 mol) of triethylamine were dissolved in 250 ml of dichloromethane, and after the solution was cooled to 0° C., 9.6 g (0.05 mol) of 1-ethyl-3(3-dimethylaminopropyl)carbodiimide·HCl was added to the solution, and the solution was stirred overnight. The reaction mixture was washed with a 0.1% aqueous solution of Na2CO3 and with a 0.1 N HCl solution, and was dried over anhydrous sodium sulfate. Dichloromethane was removed from the mixture under reduced pressure to obtain p-acetoxybenzoylglycyl-L-tyrosine ethyl ester.

Workup

  1. washThe reaction mixture was washed with a 0.1% aqueous solution of Na2CO3 and with a 0.1 N HCl solution
  2. dry with materialwas dried over anhydrous sodium sulfate
  3. customDichloromethane was removed from the mixture under reduced pressure

Sources & evidence

ORD record
ord-9d2b3f3c50f1402a9f94bc52b809bcfb
Source dataset
uspto-grants-1985_11
Patent number
US04551272

Reaction notes

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