1,2-Dichloroethane → HCID 69821478, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:5][CH:4]=1.C(N(CC)CC)C.C(Cl)CCl.[NH2:26][C@@H:27]([CH2:36][N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)[C@H:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[OH:29]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][C:12]([NH:26][C@@H:27]([CH2:36][N:37]2[CH2:38][CH2:39][O:40][CH2:41][CH2:42]2)[C@H:28]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[OH:29])=[O:14])=[CH:7][CH:8]=1Participants
6
Procedure
Methylene chloride (10 ml), 4-(4-methoxyphenyl)butanoic acid (388.0 mg, 2.0 mmol), triethylamine (0.70 ml, 5.0 mmol) and EDC (580 mg, 3.0 mmol) were added to (1S,2S)-2-amino-3-morpholino-1-phenyl-1-propanol (472.0 mg, 2.0 mmol), followed by stirring overnight. Methylene chloride (100 ml) was added to the reaction solution. After washed with a saturated sodium hydrogen carbonate solution (50 ml), water (50 ml) and saturated brine (50 ml) successively, the organic layer was dried over sodium sulfate and filtered, and the solvent was evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (chloroform:ethanol=20:1) to obtain the title compound (549 mg, yield 66%) as colorless oil.
Workup
- washAfter washed with a saturated sodium hydrogen carbonate solution (50 ml), water (50 ml) and saturated brine (50 ml) successively
- dry with materialthe organic layer was dried over sodium sulfate
- filtrationfiltered
- customthe solvent was evaporated under reduced pressure
- customThe resulting crude product was purified by silica gel column chromatography (chloroform:ethanol=20:1)
Sources & evidence
- ORD record
- ord-b04c55622f534f38b9fb8bc490f9daf4
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06407064B2
Reaction notes
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