1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 70040170, compound

HRID 485581Notes

Reaction equation

HRID 485581 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:25]([OH:27])=O)[CH2:10][CH2:11][CH2:12][CH:13]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:29]([O:36][C:37](=[O:43])[C@@H:38]1[CH2:42][CH2:41][CH2:40][NH:39]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH2:29]([O:36][C:37](=[O:43])[C@@H:38]1[CH2:42][CH2:41][CH2:40][N:39]1[C:25](=[O:27])[C@H:9]([CH2:10][CH2:11][CH2:12][CH:13]([C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[NH2:14])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2733413Proline benzyl ester hydrochlorideHCID 22798350HCID 22798350, compound

Product 1

HCID 70040170HCID 70040170, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

All the obtained oily t-butyloxycarbonyl-ε-carbobenzoxy-L-lysine and L-proline benzylester hydrochloride (4.3 g, 17.8 m mole) were dissolved in methylene dichloride and WSC (3.3 ml, 17.8 m mole) was added thereto while cooling to -15° C. The mixture was stirred overnight and the methylene dichloride was distilled off under reduced pressure. The residue was dissolved in ethyl acetate. The ethyl acetate solution was washed with 1N hydrochloric acid, 5% sodium bicarbonate and water in order, and dried with anhydrous sodium sulfate. The ethyl acetate was distilled off under reduced pressure to obtain an oily t-butyloxycarbonyl-ε-carbobenzoxy-L-lysyl-L-proline benzylester.

Workup

  1. distillationthe methylene dichloride was distilled off under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe ethyl acetate solution was washed with 1N hydrochloric acid, 5% sodium bicarbonate and water in order
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationThe ethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0b3526d3118e4b56b282bc31cc1af352
Source dataset
uspto-grants-1985_08
Patent number
US04536395

Reaction notes

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