Hydrochloric Acid → HCID 68194317, compound
Reaction equation
[C:1]([O:4][CH:5](SC)[C:6](=[O:26])[C@@H:7]([NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2].[BH4-].[Na+].Cl>CCO.O>[C:1]([O:4][CH2:5][CH:6]([OH:26])[C@@H:7]([NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -20 °C
Procedure
To a suitable reactor was added crude 3b in EtOH (100 mL) solution at 20-30° C. under N2. The mixture was cooled to −25 to −15° C., and NaBH4 (0.77 g) in H2O (7.7 mL) was added at below −8° C. The reaction mixture was warmed to −10 to −5° C. and stirred for 2 hr. The reaction was deemed completed as determined by TLC. 1N HCl aqueous solution (20 mL) was added at below 10° C. The mixture was extracted with EtOAc (100 mL×2). The separated organic portions were combined and concentrated under at 40-50° C. reduced pressure to afford crude 4b. The diastereomeric ratio of crude 4b was determined to be 97/3 by HPLC analysis.
Workup
- temperatureThe reaction mixture was warmed to −10 to −5° C.
- extractionThe mixture was extracted with EtOAc (100 mL×2)
- concentrationconcentrated under at 40-50° C. reduced pressure
Sources & evidence
- ORD record
- ord-d25666b6859745abb0e83d906dd713b6
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722921B2
Reaction notes
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