Dichloromethane → HCID 22875137, compound
Reaction equation
[CH3:1][S:2]([N:5]1[C:44]2[C:39](=[CH:40][C:41]([F:45])=[CH:42][CH:43]=2)[C:7]2([CH2:12][CH2:11][N:10]([C:13]([C@H:15]([NH:25][C:26](=[O:38])[C:27]([NH:30]C(OC(C)(C)C)=O)([CH3:29])[CH3:28])[CH2:16][O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:14])[CH2:9][CH2:8]2)[CH2:6]1)(=[O:4])=[O:3].FC(F)(F)C(O)=O.[Cl:53]CCl>>[ClH:53].[CH3:1][S:2]([N:5]1[C:44]2[C:39](=[CH:40][C:41]([F:45])=[CH:42][CH:43]=2)[C:7]2([CH2:12][CH2:11][N:10]([C:13]([C@H:15]([NH:25][C:26](=[O:38])[C:27]([NH2:30])([CH3:29])[CH3:28])[CH2:16][O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:14])[CH2:9][CH2:8]2)[CH2:6]1)(=[O:4])=[O:3]Participants
4
Procedure
To a solution of 0.101 g the intermediate from Step C in 1 mL of dichloromethane was added 1.0 mL of trifluoroacetic acid and maintained at RT for 30 min. The reaction mixture was evaporated to dryness, basified with 10% aqueous sodium carbonate solution (10 mL), and extracted with dichloromethane (3×5 mL). The combined organics were washed with brine (5 mL), dried over potassium carbonate, and concentrated. This material was dissolved in 2 mL of ethyl acetate and 0.10 mL of 4M HCl in EtOAc was added at 0° C. The precipitate was filtered under nitrogen and washed with EtOAc/ether (1:1) and dried to give 62 mg of the product as a white solid.
Workup
- customThe reaction mixture was evaporated to dryness
- extractionextracted with dichloromethane (3×5 mL)
- washThe combined organics were washed with brine (5 mL)
- dry with materialdried over potassium carbonate
- concentrationconcentrated
- dissolutionThis material was dissolved in 2 mL of ethyl acetate
- addition0.10 mL of 4M HCl in EtOAc was added at 0° C
- filtrationThe precipitate was filtered under nitrogen
- washwashed with EtOAc/ether (1:1)
- customdried
Sources & evidence
- ORD record
- ord-9c2396327b474b248f1f35df8bc35c30
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05652235
Reaction notes
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