Trimethylphosphine → HCID 86726386, compound
Reaction equation
[N:1]([C@@H:4]([C@@H:40]([C:47]1[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[C:49]([Cl:55])[CH:48]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:5]([NH:7][C:8]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:9]=1[CH2:10][CH2:11][C@H:12]1[O:17][CH2:16][C@@H:15]([CH2:18][O:19][C:20](=[O:27])[NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])[N:14]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:13]1)=[O:6])=[N+]=[N-].CP(C)C>CCOC(C)=O.O>[NH2:1][C@@H:4]([C@@H:40]([C:47]1[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[C:49]([Cl:55])[CH:48]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[C:5]([NH:7][C:8]1[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[C:9]=1[CH2:10][CH2:11][C@H:12]1[O:17][CH2:16][C@@H:15]([CH2:18][O:19][C:20](=[O:27])[NH:21][CH2:22][C:23]([F:26])([F:25])[F:24])[N:14]([C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])[CH2:13]1)=[O:6]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of the product from step 2 (160 mg, 0.20 mmol) in EtOAc (8 mL) and water (2 mL), was added trimethylphosphine (1.0 mL, 1M solution in THF, 1.0 mmol). The reaction mixture was stirred at ambient temperature for 2 h, then diluted with water (20 mL) and extracted with EtOAc (25 mL×3). The combined organic extracts were washed with brine (25 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to provide the title compound as colorless oil. (M+H)+=767.
Workup
- extractionextracted with EtOAc (25 mL×3)
- washThe combined organic extracts were washed with brine (25 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-c5f3d3b4fe8a4129af8fbfd54e676f15
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315475B2
Reaction notes
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