Benzyloxycarbonyl-L-phenylalanine → HCID 131722550, compound

HRID 1976616Notes

Reaction equation

HRID 1976616 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:23]([CH3:33])[CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27].ON1C(=O)C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([N:23]([CH3:33])[CH2:24][CH2:25][C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14760311Tert-butyl 3-(methylamino)propanoate

Product 1

HCID 131722550HCID 131722550, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

Z-Phe-OH (29.9 g, 100 mmol), MeβAla-O-t-Bu (16.0 g, 110 mmol), and 3-hydroxy-4-oxo-3,4-dihydro-1,2,3-benzotriazine (17.9 g, 110 mmol) was dissolved in methylene chloride (200 ml). This solution was cooled to −10° C., added with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (21.1 g, 110 mmol), and then stirred at −10° C. for one hour and further at room temperature for 20 hours. After the solvent was evaporated under reduced pressure, the reaction mixture was added with ethyl acetate (100 ml), and washed with 1N hydrochloric acid and then with saturated aqueous sodium hydrogencarbonate. The solvent was concentrated under reduced pressure to obtain an oily product, which was purified by silica gel column chromatography (benzene: ethyl acetate=10:1 (v/v)) to obtain 42.6 g of Z-Phe-MeβAla-O-t-Bu as a colorless oily product.

Workup

  1. customAfter the solvent was evaporated under reduced pressure
  2. additionthe reaction mixture was added with ethyl acetate (100 ml)
  3. washwashed with 1N hydrochloric acid
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customto obtain an oily product, which
  6. customwas purified by silica gel column chromatography (benzene: ethyl acetate=10:1 (v/v))

Sources & evidence

ORD record
ord-8148792f8540419c8001546670b60369
Source dataset
uspto-grants-2001_05
Patent number
US06228841B1

Reaction notes

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