Diisopropylethylamine → 4-[9-(2,5-Dioxopyrrolidin-1-yloxycarbonyl)nonyloxy]benzoic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:26])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.CN(C(O[N:44]1[C:49](=[O:50])[CH2:48][CH2:47][C:45]1=[O:46])=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[C:1]([O:5][C:6](=[O:26])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][N:44]2[C:49](=[O:50])[CH2:48][CH2:47][C:45]2=[O:46])=[O:24])=[CH:9][CH:8]=1)([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
4-(9-Carboxynonyloxy)benzoic acid tert-butyl ester (779 mg, 2.14 mmol) was dissolved in THF (15 mL), and DIEA (366 μl, 2.14 mmol) was added. The mixture was cooled to 0° C., and placed under nitrogen, and HSTU was added. The mixture was stirred at 0° C. for 30 min and at RT for 16 h. The sample was concentrated under vacuum and AcOEt (40 ml) was added. The mixture was washed with 0.2 N HCl (2×25 ml), dried over MgSO4, and concentrated under vacuum to yield a slightly yellow solid. The solid was recrystallized from AcOEt to yield a white powder (276 mg, 28% yield). The mother liquor was concentrated to yield crystalline residue (430 mg, 43% yield). Data for the white powder:
Workup
- concentrationThe sample was concentrated under vacuum and AcOEt (40 ml)
- additionwas added
- washThe mixture was washed with 0.2 N HCl (2×25 ml)
- dry with materialdried over MgSO4
- concentrationconcentrated under vacuum
- customto yield a slightly yellow solid
- customThe solid was recrystallized from AcOEt
Sources & evidence
- ORD record
- ord-fae56583379346639d98ca19143fab91
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08933021B2
Reaction notes
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