Hydrogen chloride-ethyl acetate → HCID 117987520, compound

HRID 1486674Notes

Reaction equation

HRID 1486674 reaction equation
[NH2:1][C@@:2]1([C:19]([OH:21])=[O:20])[C@@H:7]([F:8])[CH2:6][C@@H:5]2[C@H:3]1[C@H:4]2[C:9]([O:11][CH:12]([O:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH3:13])=[O:10].C(OCC)(=O)C.[ClH:28]>C(OCC)(=O)C>[ClH:28].[NH2:1][C@@:2]1([C:19]([OH:21])=[O:20])[C@@H:7]([F:8])[CH2:6][C@@H:5]2[C@H:3]1[C@H:4]2[C:9]([O:11][CH:12]([O:14][CH2:15][CH:16]([CH3:17])[CH3:18])[CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 117987521HCID 117987521, compound

Product 1

HCID 117987520HCID 117987520, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(1S,2S,3S,5R,6S)-3′-Allyl 6-(1-(isobutyryloxy)ethyl) 3-fluoro-5′-oxospiro[bicyclo[3.1.0]hexan-2,4′-oxazolidine]-3′,6-dicarboxylate (A-8-1, 403 mg) was treated in the same manner as in Example A-1 (4) to give a pale yellow oil (278 mg) containing (1S,2S,3S,5R,6S)-2-amino-3-fluoro-6-((1-(isobutyloxy)ethoxy)carbonyl)bicyclo[3.1.0]hexane-2-carboxylic acid. To the obtained oil, ethyl acetate (3 mL) was added, the mixture was stirred and then a 4 mol/L hydrogen chloride-ethyl acetate solution (3 mL) was added while cooling on ice. The mixture was stirred at room temperature for 30 minutes, then concentrated under reduced pressure and dried to give the title compound (A-8, 200 mg) as a pale yellow solid.

Workup

  1. temperaturewhile cooling on ice
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. concentrationconcentrated under reduced pressure
  4. customdried

Sources & evidence

ORD record
ord-790371dd9ea140ebb9c133171b0b87df
Source dataset
uspto-grants-2016_08
Patent number
US09428483B2

Reaction notes

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