Diisopropylethylamine → HCID 58079444, compound
Reaction equation
[C:1]([O:5][C:6](=[O:38])[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:10]([OH:12])=[O:11])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(O[N:61]1[C:66](=[O:67])[CH2:65][CH2:64][C:62]1=[O:63])=[N+](C)C)C>C1COCC1>[O:63]=[C:62]1[CH2:64][CH2:65][C:66](=[O:67])[N:61]1[O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:15]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[C:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:38])[CH:8]=1Participants
5
Conditions
- Temperature
- 0 °C
Procedure
4-(14-tert-Butoxycarbonyl tetradecyloxy)isophthalic acid 3-tert-butyl ester (0.15 g, 0.28 mmol) was dissolved in THF (2 ml). DIEA (58 μl, 0.34 mmol) was added, and the solution was cooled to 0° C. TSTU (0.10 g, 0.28 mmol) was added. The reaction was stirred at 0° C. for 30 min and then at rt for 16 h. The sample was concentrated under vacuum to near dryness. AcOEt (20 ml) was added and the solution was washed with 0.2 N HCl and sat. NaHCO3 (3×5 ml each), dried over MgSO4 and concentrated to yield a residue (0.18 g). The residue was purified by flash chromatography (silica: AcOEt/heptane 3:7 (0.5 l), 1:1 (0.2 l)) yielding an oil with white solids (55 mg, 31%).
Workup
- waitat rt for 16 h
- concentrationThe sample was concentrated under vacuum
- additionAcOEt (20 ml) was added
- washthe solution was washed with 0.2 N HCl and sat. NaHCO3 (3×5 ml each)
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-afcf8460650647fa9e87b0a345e0c4a1
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067362B2
Reaction notes
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