p-Toluenesulfonic acid → (S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester

HRID 129988Notes

Reaction equation

HRID 129988 reaction equation
[NH2:1][C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[CH3:17][C:18]1C=[CH:20][C:21](S(O)(=O)=O)=[CH:22][CH:23]=1.C1N=C[N:30]([C:33](N2C=NC=C2)=[O:34])C=1.N1CCCCCC1>C1COCC1.O>[CH2:10]([O:9][C:7](=[O:8])[C@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[NH:1][C:33]([N:30]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:18][CH2:17]1)=[O:34])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8119AzepaneHCID 682631,1'-CarbonyldiimidazoleHCID 6451313Benzyl L-leucinate

Product 1

HCID 10593708(S)-2-[(azepane-1-carbonyl)-amino]-4-methyl-pentanoic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

TEA (0.73 ml) was added dropwise to a suspension of Leu-OBzl.TsOH (1.97 g) and CDI (0.85 g) in THF (10 ml) at 0°~5° C. over a period of 5 min and the mixture was stirred at the same temperature for 1 h. Perhydroazepine (0.67 ml) was added and the reaction mixture was stirred at room temperature for 14 h, and poured into water (100 ml). The resulting precipitate was collected by filtration to afford the product (1.75 g).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 14 h
  2. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-843592f2bf9a44f9a4d58a00b072f452
Source dataset
uspto-grants-1995_11
Patent number
US05470833

Reaction notes

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