Triethylamine → HCID 14699642, compound

HRID 974183Notes

Reaction equation

[C@H:1]12[CH2:8][CH2:7][CH2:6][C@H:5]1[CH2:4][C@@H:3]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[NH:2]2.[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[CH2:29][CH2:30][CH2:31][C:32](O)=[O:33].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[CH:19]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[CH:21][C:20]=1[CH2:29][CH2:30][CH2:31][C:32]([N:2]1[C@H:3]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:4][C@H:5]2[C@@H:1]1[CH2:8][CH2:7][CH2:6]2)=[O:33]

Participants

Conditions

Temperature: -5 °C

Procedure

2 5 g of benzyl (lS,3S,5S)-2-azabicyclo[3.3.0]octane-3-carboxylate and 2.2 g of 4-(2-naphthyl)butyric acid are dissolved in 40 ml of DMF and cooled to -5° C. 7.7 ml of triethylamine and then 10 ml of n-propylphosphonic anhydride (50 % strength solution in dichloromethane) were pipetted into this solution under a nitrogen atmosphere. This mixture was stirred at room temperature for 48 hours, to effect complete conversion. The solution was diluted with 100 ml of ethyl acetate and successively extracted two times each with saturated NaHCO3 solution, 10 % strength citric acid solution and saturated NaCl solution. After drying over MgSO4 and concentration of the organic phase, the crude product obtained was separated by column chromatography over silica gel (cyclohexane/ethyl acetate). This gave 2.52 g of the desired product.

Workup

extractionsuccessively extracted two times each with saturated NaHCO3 solution, 10 % strength citric acid solution and saturated NaCl solution
dry with materialAfter drying over MgSO4 and concentration of the organic phase

Sources & evidence

ORD record: ord-6246d4c35e044638af0b8a135161867a
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05068242

Reaction notes

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