Triethylamine → N-(t-butyloxycarbonyl)-4-phenacyloxy-L-phenylalanine cyclohexylamide

HRID 330429Notes

Reaction equation

HRID 330429 reaction equation
[CH:1]1([NH:7][C:8](=[O:26])[C@H:9]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N([CH2:32][CH3:33])CC)C.C(Cl)(=O)[O:35][CH2:36][CH3:37].N[C:41]1[CH:46]=CN=[C:43](Cl)[CH:42]=1>O1CCCC1>[CH:1]1([NH:7][C:8](=[O:26])[C@H:9]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:37][C:36]([C:33]3[CH:32]=[CH:43][CH:42]=[CH:41][CH:46]=3)=[O:35])=[CH:21][CH:20]=2)[NH:10][C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 844322-Chloropyridin-4-amineHCID 131716286t-butyloxycarbonyl-4-hydroxy-L-phenylalanine cyclohexylamide

Product 1

HCID 70070014N-(t-butyloxycarbonyl)-4-phenacyloxy-L-phenylalanine cyclohexylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine (I) (4.46 g) was dissolved in dry tetrahydrofuran (110 ml) and triethylamine (1.80 ml) was added under ice-cooling, followed by stirring for 15 minutes. To this solution was added ethyl chlorocarbonate (1.44 g) and the mixture was stirred for 30 minutes. After adding 4-amino-2-chloropyridine (1.54 g), the reaction was carried out at room temperature for 10 hours. The solid was filtered off and the filtrate was concentrated under a reduced pressure. The residue was extracted with ethyl acetate. The extract was purified with a column chromatography to obtain N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine 4-(2-chloro)pyridylamide (II) (0.60 g). Following the procedure of Example 7, the final compound N-(trans-4-aminomethylcyclohexylcarbonyl)-4-benzyloxy-L-phenylalanine 4-(2-chloro)pyridylamide hydrochloride (III) (0.67 g) was obtained from the compound (II).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 30 minutes
  3. waitthe reaction was carried out at room temperature for 10 hours
  4. filtrationThe solid was filtered off
  5. concentrationthe filtrate was concentrated under a reduced pressure
  6. extractionThe residue was extracted with ethyl acetate
  7. customThe extract was purified with a column chromatography

Sources & evidence

ORD record
ord-53e562656b904a4db1fca7f0d227b376
Source dataset
uspto-grants-1990_01
Patent number
US04895842

Reaction notes

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