Reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:36])[N:21]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])=O)(C)(C)C>C(Cl)Cl>[CH2:29]([O:28][N:21]([C:20](=[O:36])[CH2:19][CH2:18][CH2:17][CH2:16][NH:15][O:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[N:27])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
Trifluoroacetic acid (25 mL) was slowly dripped into a solution of (4) (7.10 g, 13.93 mmol) in CH2Cl2 (150 mL) which had been cooled to 0° C. The solution was stirred at 0° C. for 30 minutes and at room temperature for 15 minutes. Solvent and excess TFA were removed by rotary evaporation, and the concentrate was cooled to 0° C., treated with saturated NaHCO3 (150 mL) and extracted with CH2Cl2 (4×80 mL). After solvent removal, the crude oil was purified by silica gel column chromatography with 1:1 hexane/EtOAc as the eluant, generating 4.6 g (81%) of (5) as an oil: NMR δ 1.40-190 (m, 8 H), 2.30 (t, 2 H, J=6), 2.40 (t, 2 H, J=6), 2.90 (t, 2 H, J=6), 3.63 (t, 2 H, J=6), 4.63 (s, 2 H), 4.75 (s, 2 H), 4.93 (br s, 1 H), 7.27 (s, 5 H), 7.33 (s, 5 H). Anal. (C24H31N3O3) C, H, N.
Workup
- customSolvent and excess TFA were removed by rotary evaporation
- temperaturethe concentrate was cooled to 0° C.
- additiontreated with saturated NaHCO3 (150 mL)
- extractionextracted with CH2Cl2 (4×80 mL)
- customAfter solvent removal
- customthe crude oil was purified by silica gel column chromatography with 1:1 hexane/EtOAc as the eluant
Sources & evidence
- ORD record
- ord-63b160e7ff22430e9ce2464bfd8afded
- Source dataset
- uspto-grants-1994_06
- Patent number
- US05322961
Linked notes
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