Phenylacetic Acid → HCID 22103484, compound
Reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[CH3:17][C:18]1[C:22]([CH3:23])=[C:21]([N:24]([CH2:49][O:50][CH2:51][CH2:52][O:53][CH3:54])[S:25]([C:28]2[C:29]([C:34]3[CH:39]=[CH:38][C:37]([C:40]4[O:41][CH:42]=[CH:43][N:44]=4)=[CH:36][C:35]=3[CH2:45][CH2:46][NH:47][CH3:48])=[CH:30][CH:31]=[CH:32][CH:33]=2)(=[O:27])=[O:26])[O:20][N:19]=1.CCN(CC)CC>C(Cl)Cl.CN(C=O)C>[CH3:17][C:18]1[C:22]([CH3:23])=[C:21]([N:24]([CH2:49][O:50][CH2:51][CH2:52][O:53][CH3:54])[S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[C:34]2[CH:39]=[CH:38][C:37]([C:40]3[O:41][CH:42]=[CH:43][N:44]=3)=[CH:36][C:35]=2[CH2:45][CH2:46][N:47]([CH3:48])[C:8](=[O:10])[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:27])=[O:26])[O:20][N:19]=1Participants
7
Procedure
To phenylacetic acid (7.9 mg, 0.058 mmol) and 0.003 ml DMF in 1 ml CH2Cl2, oxalyl chloride (2M in CH2Cl2, 0.073 ml, 0.15 mmol) was added. The mixture was stirred at room temperature for 1.5 hr and concentrated. The residue was dissolved in 0.5 ml CH2Cl2 and cooled to 0° C. A solution of the title compound of Step (A) (29 mg, 0.053 mmol) in 0.5 ml CH2Cl2 was added and followed by Et3N (16 mg, 0.16 mmol). The reaction was stirred at room temperature for 2 hr and concentrated to give the title compound of this step.
Workup
- concentrationconcentrated
- dissolutionThe residue was dissolved in 0.5 ml CH2Cl2
- temperaturecooled to 0° C
- stirringThe reaction was stirred at room temperature for 2 hr
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-2fc68e88f1a54f7ea490225f8aa85ffa
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05846990
Reaction notes
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