Triethylamine → BOC-p-nitrophenylalanine 2-oxopropyl amide

HRID 5751Notes

Reaction equation

HRID 5751 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:20]([OH:22])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:24][CH2:25][C:26](=[O:28])[CH3:27].C(N(CC)CC)C.ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C.C(O)(=O)C>[O:28]=[C:26]([CH3:27])[CH2:25][NH:24][C:20](=[O:22])[C@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 30840252-Propanone, 1-amino-, hydrochlorideHCID 7021882N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanine

Product 1

HCID 18632424BOC-p-nitrophenylalanine 2-oxopropyl amide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

t-Butyloxycarbonyl-p-nitrophenylalanine (4.42 g, 14.26 mmol, aminoacetone hydrochloride (1.56 g, 14.26 mmol), triethylamine (1.44 g, 14.26 mmol), 1-hydroxybenzotriazole (1.69 g, 12.55 mmol), were dissolved in ethyl acetate (400 ml). 1,3-Dicyclohexylcarbodiimide (3.23 g, 15.68 mmol) in ethyl acetate (25 ml) was added and the solution allowed to stir for 18 hours. Glacial acetic acid (0.2 ml) was added and the solution was filtered. The filtrate was extracted with saturated salt solution (100 ml), 1N HCl solution (3×100 ml), saturated salt solution (100 ml), 5% bicarbonate solution (3×100 ml), and saturated salt solution (100 ml). The organic phase was dried over MgSO4, filtered and concentrated to 50 ml. Petroleum ether (50 ml) was added and the solution was cooled to 0° C. for 12 hours. The precipitated product was collected and dried under vacuum.

Workup

  1. filtrationthe solution was filtered
  2. extractionThe filtrate was extracted with saturated salt solution (100 ml), 1N HCl solution (3×100 ml), saturated salt solution (100 ml), 5% bicarbonate solution (3×100 ml), and saturated salt solution (100 ml)
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to 50 ml
  6. additionPetroleum ether (50 ml) was added
  7. customThe precipitated product was collected
  8. customdried under vacuum

Sources & evidence

ORD record
ord-777c1fb9b65b4cdf9d3f220923205cdd
Source dataset
uspto-grants-1993_09
Patent number
US05246692

Reaction notes

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