Triethylamine → HCID 53926994, compound

HRID 1155084Notes

Reaction equation

HRID 1155084 reaction equation
[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=O.C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:34]([NH2:44])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>CN(C=O)C>[N:1]1([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([NH:44][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[O:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8916DecylamineHCID 62365Isobutyl chloroformateHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 53926994HCID 53926994, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

5.0 g (20 mmoles) of Z-Pro-OH are dissolved in 50 ml of DMFA, 2.8 ml (20 mmoles) of triethylamine are added to the solution, and the mixture is cooled to -10° C. The mixture is stirred at the same temperature, 2.8 ml (21.5 mmoles) of isobutyl chloroformate are added dropwise, and after 10 minutes 4.4 ml (22 mmoles) of n-decylamine are introduced dropwise. After the addition the reaction mixture is stirred at 0° C. for 30 minutes and then at room temperature for 2 hours. The resulting suspension is filtered, the filtrate is evaporated, and the residue is dissolved in 100 ml of ethyl acetate. The solution is shaken four times with 50 ml of n hydrochloric acid, each, twice with 50 ml of n sodium hydrocarbonate solution, each, and then with 50 ml of water, dried over anhydrous sodium sulfate and evaporated. The oily residue is crystallized from n-hexane to obtain 5.43 g (70%) of Z-Pro-NH-C10H21 ; m.p.: 78°-80° C., Rf2 =0.75.

Workup

  1. additionare added dropwise
  2. additionAfter the addition the reaction mixture
  3. waitat room temperature for 2 hours
  4. filtrationThe resulting suspension is filtered
  5. customthe filtrate is evaporated
  6. dissolutionthe residue is dissolved in 100 ml of ethyl acetate
  7. stirringThe solution is shaken four times with 50 ml of n hydrochloric acid
  8. dry with materialeach, twice with 50 ml of n sodium hydrocarbonate solution, each, and then with 50 ml of water, dried over anhydrous sodium sulfate
  9. customevaporated
  10. customThe oily residue is crystallized from n-hexane

Sources & evidence

ORD record
ord-418077fb76e94b50b6fefe9601acfaa0
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

Loading…