Hydrochloric Acid → HCID 86670078, compound
Reaction equation
[C:1]([O:4][CH:5](SC)[C:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:7])(=[O:3])[CH3:2].CCO.[BH4-].[Na+].Cl>O.CCOC(C)=O>[C:1]([O:4][CH2:5][CH:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[OH:7])(=[O:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -20 °C
Procedure
To a suitable reactor was added 3g (1.19 g, 1.0 equiv) and EtOH (6 mL) was added at 20-30° C. under N2. The mixture was cooled to −25 to −15° C., and NaBH4 (107.1 mg, 0.8 equiv) in H2O (2.4 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 (11 mL) was added at below 10° C., and the mixture was warmed to 20-30° C. EtOAc (100 mL) was added at 20-30° C., and the mixture was stirred at this temperature for 30 min. The separated organic portion was concentrated under reduced pressure to afford crude 4g. The diastereomeric ratio of crude 4g was determined to be 95/5 by HPLC analysis. The residue was purified by flash column chromatography (EtOAc/n-heptane=1/1) to give a diastereomeric mixture of 4g (0.84 g, 82% yield) as a yellow oil.
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 under reduced pressure
Sources & evidence
- ORD record
- ord-8f62a8db36b84d12985db536e45891ad
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722921B2
Reaction notes
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