Lithium Hydroxide → HCID 178452942, compound

HRID 929900Notes

Reaction equation

HRID 929900 reaction equation
C([O:3][C:4]([C@:6]1([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:11][C@H:10]([S:12][C:13]2[N:17]=[CH:16][NH:15][N:14]=2)[C@@H:9]2[C@H:7]1[C@H:8]2[C:18]([O:20]CC)=[O:19])=[O:5])C.[OH-].[Li+]>O1CCCC1>[C:27]([O:26][C:24]([NH:23][C@@:6]1([C:4]([OH:5])=[O:3])[CH2:11][C@H:10]([S:12][C:13]2[N:17]=[CH:16][NH:15][N:14]=2)[C@@H:9]2[C@H:7]1[C@H:8]2[C:18]([OH:20])=[O:19])=[O:25])([CH3:30])([CH3:28])[CH3:29]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 178472527HCID 178472527, compound

Product 1

HCID 178452942HCID 178452942, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To diethyl(1R,2S,4S,5R,6R)-2-tert-butoxycarbonylamino-4-(1H-[1,2,4]triazol-3-ylsulfanyl)-bicyclo[3.1.0]hexane-2,6-dicarboxylate (1.9 g, 4.31 mmol) in tetrahydrofuran (20 mL) add 2.5M aqueous solution lithium hydroxide (20.70 mL, 51.76 mmol) and stir at room temperature overnight. Evaporate the tetrahydrofuran. Dilute with water and wash with ethyl acetate. Discard the organic layer. Adjust aqueous phase to pH=2 with 5M hydrochloric acid and extract with ethyl acetate. Separate the layers and dry the organics over magnesium sulfate, filter and concentrate. The title compound is obtained as a white solid (1.58 g, 95%). MS (m/z): 385 (M+1).

Workup

  1. customEvaporate the tetrahydrofuran
  2. additionDilute with water
  3. washwash with ethyl acetate
  4. extractionextract with ethyl acetate
  5. customSeparate the layers
  6. dry with materialdry the organics over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-0164747d18c2476bb16f156a0015089d
Source dataset
uspto-grants-2016_03
Patent number
US09296710B2

Reaction notes

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