Hydrochloric Acid → HCID 60172447, compound
Reaction equation
[C:1]([O:4][CH:5](SC)[C:6](=[O:20])[C@@H:7]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH:9]([CH3:11])[CH3:10])(=[O:3])[CH3:2].CCO.[BH4-].[Na+].Cl>O.CCOC(C)=O>[C:1]([O:4][CH2:5][CH:6]([OH:20])[C@@H:7]([NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:8][CH:9]([CH3:11])[CH3:10])(=[O:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -20 °C
Procedure
To a suitable reactor was added 3f (1.55 g, 1.0 equiv) and EtOH (30 mL) was added at 20-30° C. under N2. The mixture was cooled to −25 to −15° C., and NaBH4 (132.1 mg, 0.8 equiv) in H2O (3.1 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 4f. The diastereomeric ratio of crude 4f was determined to be 58/42 by HPLC analysis. The residue was purified by flash column chromatography (EtOAc/n-heptane=1/2) to give a diastereomeric mixture of 4f (1.04 g, 78% yield) as a yellow solid.
Workup
- additionwas added at 20-30° C. under N2
- 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-e588787380284bebb31d398ef4c5354f
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722921B2
Reaction notes
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