HCID 117987479, compound → HCID 72550767, compound

HRID 1486682Notes

Reaction equation

HRID 1486682 reaction equation
C1(S(O)(=O)=O)C=CC=CC=1.[NH2:11][C@@:12]1([C:38]([OH:40])=[O:39])[C@@H:17]([F:18])[CH2:16][C@@H:15]2[C@H:13]1[C@H:14]2[C:19]([O:21][C@@H:22]([O:24][C:25]([O:27][C@@H:28]1[CH2:33][C@H:32]([CH3:34])[CH2:31][CH2:30][C@H:29]1[CH:35]([CH3:37])[CH3:36])=[O:26])[CH3:23])=[O:20]>CC(C)=O.O>[NH2:11][C@@:12]1([C:38]([OH:40])=[O:39])[C@@H:17]([F:18])[CH2:16][C@@H:15]2[C@H:13]1[C@H:14]2[C:19]([O:21][C@@H:22]([O:24][C:25]([O:27][C@@H:28]1[CH2:33][C@H:32]([CH3:34])[CH2:31][CH2:30][C@H:29]1[CH:35]([CH3:36])[CH3:37])=[O:26])[CH3:23])=[O:20]

Participants

4

Reactant 1

HCID 117987479HCID 117987479, compound

Product 1

HCID 72550767HCID 72550767, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a suspension of (1S,2S,3S,5R,6S)-2-amino-3-fluoro-6-(((S)-1-(((((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)carbonyl)oxy)ethoxy)carbonyl)bicyclo[3.1.0]hexane-2-carboxylic acid benzenesulfonate obtained in Step (4) (A-18-4, 33.0 g) in acetone (125 mL), water (25 mL) was added for dissolution. The resulting solution was added dropwise to water (1225 mL) over 30 minutes and the mixture was stirred at room temperature for 2 hours. The resulting solid was collected by filtration and washed with water (50 ml) to give the title compound (A-18, 24.08 g) as a colorless solid.

Workup

  1. additionwas added for dissolution
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water (50 ml)

Sources & evidence

ORD record
ord-78545e71945244a3b8d55bda555ebf4d
Source dataset
uspto-grants-2016_08
Patent number
US09428483B2

Reaction notes

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