Hydrochloric Acid → Hydrochloric Acid

HRID 1071828Notes

Reaction equation

HRID 1071828 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH2:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=1)[C@@H:9]([OH:16])[C@@H:10]([OH:15])[CH2:11][CH2:12][CH2:13][CH3:14])(C)(C)C.[ClH:27]>O1CCOCC1>[F:24][C:22]1[CH:23]=[C:18]([CH:19]=[C:20]([F:25])[CH:21]=1)[CH2:17][C@H:8]([NH2:7])[C@@H:9]([OH:16])[C@@H:10]([OH:15])[CH2:11][CH2:12][CH2:13][CH3:14].[ClH:27]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69746561HCID 69746561, compound

Product 2

HCID 313Hydrochloric AcidHCID 59067291HCID 59067291, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
2.5 °C

Procedure

To a cooled (0-5° C.) solution of (1S,2R,3S)-[l-(3,5-Difluoro-benzyl)-2,3-dihydroxy-heptyl]-carbamic acid tert-butyl ester (1.19 g, 3.2 mmol) in dioxane (20 mL) was added HCl (4 M in dioxane, 80 mL, 320 mmol) over 30 min. The reaction mixture was stirred at 0-5° C. for 30 min, then room temperature overnight. The volatiles were removed in vacuo and the residue was evaporated from ether to afford (1S,2R,3S)-1-(3,5-difluorobenzyl)-2,3-dihydroxyheptylamine as an HCl salt. MS (ESI+) for C14H21F2NO2 m/z 274.2 (M+H)+.

Workup

  1. customroom temperature overnight
  2. customThe volatiles were removed in vacuo
  3. customthe residue was evaporated from ether

Sources & evidence

ORD record
ord-7b3f9225dee24d5f9ae036d27f6a8b8f
Source dataset
uspto-grants-2005_06
Patent number
US06906104B2

Reaction notes

Loading…