Triethylamine → HCID 53960365, compound

HRID 1076426Notes

Reaction equation

HRID 1076426 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].C(N(CC)CC)C.C(OC(Cl)=O)C.[NH2:29][C@H:30]([C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33]>CN(C)C=O>[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([NH:29][C@H:30]([C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33])=[O:8])[CH:3]([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 83693Boc-L-ValineHCID 6451313Benzyl L-leucinate

Product 1

HCID 53960365HCID 53960365, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

19.9 g (92 mmols) of BOC-Val-OH are dissolved in 200 ml of freshly distilled dimethylformamide, while heating. After cooling to 0°C, 25.9 ml of absolute triethylamine are added and the solution cooled to -10°C before 8.64 ml of chlorocarbonic acid ethyl ester are added. After 10 minutes, a solution of 23.2 g (90 mmols) of H-Leu-OBzl, HCL in 90 ml of dimethylformamide is added at -10°C. The mixture is allowed to stand at -10°C for 30 minutes, at 0°C for 3 hours, and at 20°C for 16 hours. Undissolved matter is then filtered off and the filtrate concentrated to dryness under a high vacuum. The residue is dissolved in ethyl acetate and the solution washed with dilute citric acid solution, water, sodium bicarbonate solution, and water, dried with sodium sulfate, and evaporated. On addition of petroleum ether the product crystallizes overnight. Melting point 88.5° - 89.5°C; [α]D20 -22° (c = 2 in dimethylformamide); Rf2 = 0.73.

Workup

  1. temperaturewhile heating
  2. additionare added
  3. waitto stand at -10°C for 30 minutes, at 0°C for 3 hours
  4. waitat 20°C for 16 hours
  5. filtrationUndissolved matter is then filtered off
  6. concentrationthe filtrate concentrated to dryness under a high vacuum
  7. dissolutionThe residue is dissolved in ethyl acetate
  8. washthe solution washed with dilute citric acid solution, water, sodium bicarbonate solution, and water
  9. dry with materialdried with sodium sulfate
  10. customevaporated
  11. additionOn addition of petroleum ether the product
  12. customcrystallizes overnight

Sources & evidence

ORD record
ord-a677d611083845eb95510d4c0d8087e7
Source dataset
uspto-grants-1976_05
Patent number
US03956260

Reaction notes

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