Hydrochloric Acid → HCID 131736633, compound
Reaction equation
[Cl:1][C:2]1[C:3]([F:58])=[C:4]([C:8](=O)[CH2:9][CH2:10][N:11]([C@@H:23]2[C:39]3=[N:40][C:36](=[C:37]([CH3:49])[N:38]3[CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:35]3[C:30](=[CH:31][C:32]([NH:50][C:51](=[O:54])[O:52][CH3:53])=[CH:33][CH:34]=3)[NH:29][C:28](=[O:55])[C@H:27]([CH3:56])[CH2:26][CH2:25][CH2:24]2)[C:12](=[O:22])[CH2:13]P(OCC)(OCC)=O)[CH:5]=[CH:6][CH:7]=1.C[O-].[Na+].Cl>CO>[Cl:1][C:2]1[C:3]([F:58])=[C:4]([C:8]2[CH2:9][CH2:10][N:11]([C@@H:23]3[C:39]4=[N:40][C:36](=[C:37]([CH3:49])[N:38]4[CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:47])([CH3:46])[CH3:48])[C:35]4[C:30](=[CH:31][C:32]([NH:50][C:51](=[O:54])[O:52][CH3:53])=[CH:33][CH:34]=4)[NH:29][C:28](=[O:55])[C@H:27]([CH3:56])[CH2:26][CH2:25][CH2:24]3)[C:12](=[O:22])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a round bottom flask was added 151D (35 mg, 0.040 mmol) and MeOH (2 mL). The reaction was cooled to 0° C. and sodium methoxide (26.2 mg, 0.121 mmol) was added to the reaction. The reaction was stirred at 0° C. for 10 min. Then the reaction was quenched by 1N HCl (0.081 mL, 0.081 mmol). The reaction was then partitioned between EtOAc (25 mL) and NaHCO3 (10 mL). The organic layer was separated, washed with saturated NaCl solution (10 mL), dried over MgSO4, filtered and concentrated to give methyl 151E (22 mg, 0.031 mmol, 76% yield) as a white solid. MS (ESI) m/z: 710.3 (M+H)+.
Workup
- customThe reaction was then partitioned between EtOAc (25 mL) and NaHCO3 (10 mL)
- customThe organic layer was separated
- washwashed with saturated NaCl solution (10 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-52fef7a3bb2541d8ba4a51e10d94b144
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409908B2
Reaction notes
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