Hydrochloric Acid → HCID 86670076, compound

HRID 1024543Notes

Reaction equation

HRID 1024543 reaction equation
[C:1]([O:4][CH:5](SC)[C:6](=[O:17])[C@@H:7]([NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:8])(=[O:3])[CH3:2].CCO.[BH4-].[Na+].Cl>O.CCOC(C)=O>[C:1]([O:4][CH2:5][CH:6]([OH:17])[C@@H:7]([NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:8])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 60172442HCID 60172442, compound

Product 1

HCID 86670076HCID 86670076, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

To a suitable reactor was added 3d (2.2 g, 1.0 equiv) and EtOH (11 mL) at 20-30° C. under N2. The mixture was cooled to −25 to −15° C., and NaBH4 (304.1 mg, 0.8 equiv) in H2O (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 complete as determined by TLC. 1N HCl aqueous solution (32 mL) was added at below 10° C., and the mixture was warmed to 20-30° C. EtOAc (200 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 4d. The diastereomeric ratio of crude 4d was determined to be 72/28 by HPLC analysis. The residue was purified by flash column chromatography (EtOAc/n-heptane=1/2) to give a diastereomeric mixture of 4d (2.20 g, 83% yield) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was warmed to −5-5° C.
  2. temperaturethe mixture was warmed to 20-30° C
  3. stirringthe mixture was stirred at this temperature for 30 min
  4. concentrationThe separated organic portion was concentrated at 40-50° C. under reduced pressure

Sources & evidence

ORD record
ord-2a882ad7400e4cce870bc07a00272749
Source dataset
uspto-grants-2014_05
Patent number
US08722921B2

Reaction notes

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