3'-Aminoacetophenone → HCID 131725786, compound
Reaction equation
[OH:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:3].CN1CCOCC1.ClC(OCC(C)C)=O.[CH3:32][C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[C:37](N)[CH:36]=1)=[O:34]>CN(C=O)C>[C:33]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)(=[O:34])[CH3:32].[OH:3][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:1]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The D-biotin (1.0 gram (g), 4.1 millimoles (mmol) is solubilized in 45 milliliters (ml) of anhydrous DMF in the hot state. The mixture is cooled to 0° C. under argon, and then N-methylmorpholine (590 microliters (μl), 5.33 mmol) and isobutyl chloroformate (840 μl, 6.60 mmol) are successively added. The mixture is kept stirred for 30 minutes (min), and then 3-aminoacetophenone (824 mg, 6.10 mmol) and N-methylmorpholine (480 μl, 4.35 mmol) in 10 ml of DMF are added. The solution is maintained stirred at 0° C. for 2 hours (h), and then evaporated to dryness. The residue is taken up in 3 ml of MeOH, and then 50 ml of water are added. The precipitate obtained is filtered, washed with water, CH2Cl2 and ether to give 1.2 g (80%) of crude product 1a. Recrystallization from the MeOH—H2O pair gives 1a (1.01 g, 70%) in the form of a white powder.
Workup
- temperatureThe solution is maintained
- stirringstirred at 0° C. for 2 hours (h)
- customevaporated to dryness
- addition50 ml of water are added
- customThe precipitate obtained
- filtrationis filtered
- washwashed with water, CH2Cl2 and ether
- customto give 1.2 g (80%) of crude product 1a
- customRecrystallization from the MeOH—H2O pair
Sources & evidence
- ORD record
- ord-72d62933a61e49249fdea47ca84701a5
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07060441B2
Reaction notes
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