Hydrochloric Acid → HCID 86670077, compound
Reaction equation
[C:1]([O:4][CH:5](SC)[C:6](=[O:19])[C@@H:7]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:8]([CH3:10])[CH3:9])(=[O:3])[CH3:2].CCO.[BH4-].[Na+].Cl>O.CCOC(C)=O>[C:1]([O:4][CH2:5][CH:6]([OH:19])[C@@H:7]([NH:11][C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH:8]([CH3:10])[CH3:9])(=[O:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -20 °C
Procedure
To a suitable reactor was added 3e (1.32 g, 1.0 equiv) and EtOH (26 mL) at 20-30° C. under N2. The mixture was cooled to −25 to −15° C., and NaBH4 (117.4 mg, 0.8 equiv) in H2O (2.6 mL) was added at below −15° C. The reaction mixture was warmed to −5-5° C. and stirred for 1 hr. The reaction was deemed completed as determined by TLC. 1N HCl aqueous solution (13 mL) was added at below 10° C., and the mixture was warmed to 20-30° C. EtOAc (160 mL) was added at 20-30° C., and the mixture was stirred at this temperature for 30 min. The separated organic portion was concentrated at 40-50° C. under reduced pressure to afford crude 4e. The diastereomeric ratio of crude 4e was determined to be 78/22 by HPLC analysis. The residue was purified by flash column chromatography (EtOAc/n-heptane=1/2) to give a diastereomeric mixture of 4e (0.92 g, 81% yield) as a yellow oil.
Workup
- temperatureThe reaction mixture was warmed to −5-5° C.
- temperaturethe mixture was warmed to 20-30° C
- stirringthe mixture was stirred at this temperature for 30 min
- concentrationThe separated organic portion was concentrated at 40-50° C. under reduced pressure
Sources & evidence
- ORD record
- ord-1fa4c85f3afd4e27a509dea566eadab3
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722921B2
Reaction notes
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