Hydrochloric Acid → HCID 59571235, compound
Reaction equation
Cl.[NH2:2][C@@H:3]1[C:17](=[O:18])[N:16]2[CH2:19][C@@H:20]([O:22][S:23]([C:26]3[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH2:21][C@H:15]2[C:14](=[O:33])[NH:13][C@:12]2([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:34][C@H:11]2[CH:10]=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CCN(CC)CC.[CH2:47]([C@@H:52]1[CH2:56][CH2:55][CH2:54][C@H:53]1[O:57][C:58](ON1C(=O)CCC1=O)=[O:59])[CH2:48][CH2:49][CH:50]=[CH2:51].Cl>CC#N.CCOC(C)=O>[Br:32][C:29]1[CH:28]=[CH:27][C:26]([S:23]([O:22][C@@H:20]2[CH2:19][N:16]3[C:17](=[O:18])[C@@H:3]([NH:2][C:58]([O:57][C@@H:53]4[CH2:54][CH2:55][CH2:56][C@H:52]4[CH2:47][CH2:48][CH2:49][CH:50]=[CH2:51])=[O:59])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=[CH:10][C@@H:11]4[CH2:34][C@@:12]4([C:35]([O:37][CH2:38][CH3:39])=[O:36])[NH:13][C:14](=[O:33])[C@@H:15]3[CH2:21]2)(=[O:25])=[O:24])=[CH:31][CH:30]=1Participants
7
Procedure
To a solution of the compound from Step 1 (300 mg, 0.46 mmol) in MeCN (0.5 mL) was added Et3N (0.19 mL, 1.36 mmol). A solution of the compound from Step 2 (150 mg, 0.51 mmol) in MeCN (1.5 mL) was added, and the reaction mixture was stirred at RT for 1 hour. The reaction mixture was worked up with EtOAc and 1M HCl, and the organics were washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by silica gel chromatography (gradient elution 0 to 100% EtOAc in hexane). LCMS (M+H)+=792.0.
Workup
- washthe organics were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe crude material was purified by silica gel chromatography (gradient elution 0 to 100% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-1d7746c050414218b11cd3fa2b0cee78
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08377874B2
Reaction notes
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