Lithium Hydroxide → HCID 178453814, compound

HRID 929899Notes

Reaction equation

HRID 929899 reaction equation
C([O:3][C:4]([C@:6]1([NH:23][C:24](=[O:34])[CH2:25][NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:11][C@H:10]([S:12][C:13]2[NH:17][CH:16]=[N: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.O>[C:30]([O:29][C:27]([NH:26][CH2:25][C:24]([NH:23][C@@:6]1([C:4]([OH:5])=[O:3])[CH2:11][C@H:10]([S:12][C:13]2[NH:17][CH:16]=[N:15][N:14]=2)[C@@H:9]2[C@H:7]1[C@H:8]2[C:18]([OH:20])=[O:19])=[O:34])=[O:28])([CH3:33])([CH3:31])[CH3:32]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178472525HCID 178472525, compound

Product 1

HCID 178453814HCID 178453814, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve diethyl(1R,2S,4S,5R,6R)-2-[[-2-(tert-butoxycarbonylamino) acetyl]amino]-4-(4H-1,2,4-triazol-3-ylsulfanyl)bicyclo[3.1.0]hexane-2,6-dicarboxylate (0.420 g, 0.84 mmol) in tetrahydrofuran (7 mL) then add 2.5M lithium hydroxide (6.7 mL, 16.88 mmol). Stir the mixture at room temperature for 3.5 hours. Dilute the reaction mixture with water and wash with ethyl acetate. Discard the organic layer. Adjust the aqueous phase to pH=2 with 1N hydrochloric acid and extract with ethyl acetate. Dry the organic phase over magnesium sulfate, filter and concentrate to dryness to yield the title compound as a white solid (250 mg, 66%). MS (m/z): 442 (M+1), 464 (M+23).

Workup

  1. washwash with ethyl acetate
  2. extractionextract with ethyl acetate
  3. dry with materialDry the organic phase over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-1cc9cfdd69e0496980fe9093a3faabcf
Source dataset
uspto-grants-2016_03
Patent number
US09296710B2

Reaction notes

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