Hydrochloric Acid → HCID 89813085, compound

HRID 1481077Notes

Reaction equation

HRID 1481077 reaction equation
C([C@H]1[O:9][C@:8]([CH2:11][NH:12]C(=O)OC)([CH3:10])[C:7](=[O:17])[O:6]1)(C)(C)C.[ClH:18]>O>[ClH:18].[NH2:12][CH2:11][C@@:8]([OH:9])([CH3:10])[C:7]([OH:17])=[O:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131736617HCID 131736617, compound

Product 1

HCID 89813085HCID 89813085, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
115 °C

Procedure

Methyl ((2S,4S)-2-tert-butyl-4-methyl-5-oxo-1,3-dioxolan-4-yl)methylcarbamate (310 mg, 1.27 mmol) (Huang et al. (2006) Tetrahedron: Asymmetry 17(22):3152-3157) was suspended in 6 N HCl (12.7 mL) in a sealed tube. The resulting mixture was heated at 110-120° C. for 16 hours and then cooled to room temperature. The reaction crude was diluted with H2O (12 mL) and then extracted twice with EtOAc. The aqueous layer was concentrated to give the title compound in 187 mg, which was used directly in the subsequent step without further purification.

Workup

  1. temperaturecooled to room temperature
  2. customThe reaction crude
  3. extractionextracted twice with EtOAc
  4. concentrationThe aqueous layer was concentrated

Sources & evidence

ORD record
ord-c7d2661d8cdd4a4dbd2ee6e60194f078
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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