Diisopropylethylamine → HCID 68088438, compound
Reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:29])[N:5]([C@@H:12]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH3:28])[CH:19]=1)[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:6]2=[O:11].C(N(C(C)C)CC)(C)C.[CH2:39]([O:46][CH2:47][C:48](Cl)=[O:49])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[CH2:39]([O:46][CH2:47][C:48]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:29])[N:5]([CH:12]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH3:28])[CH:19]=1)[CH2:13][S:14]([CH3:17])(=[O:15])=[O:16])[C:6]2=[O:11])=[O:49])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22.5 °C
Procedure
To a solution of (1S)-4-amino-2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-isoindole-1,3-dione (1.0 g, 2.4 mmol) in methylene chloride (20 mL), was added diisopropyl ethylamine (0.45 mL, 2.6 mmol), followed by benzyloxy-acetyl chloride (0.37 mL, 2.4 mmol) at 0° C. After 1 hour, the mixture was allowed to warm to 20-25° C. After 15 minutes, the mixture was cooled back to 0° C. To the cooled mixture, was added diisopropyl ethylamine (0.18 mL), and benzyloxy-acetyl chloride (0.14 mL). After 2 hours, the mixture was concentrated, and the resulting residue was purified by Silica Gel column chromatograph to give (1S) 2-benzyloxy-N-{2-[1-(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}-acetamide (1.2 g, 88% yield).
Workup
- waitAfter 15 minutes
- temperaturethe mixture was cooled back to 0° C
- waitAfter 2 hours
- concentrationthe mixture was concentrated
- customthe resulting residue was purified by Silica Gel column chromatograph
Sources & evidence
- ORD record
- ord-75c1c0280ba84b18b790cbd621db1ceb
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853175B2
Reaction notes
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