Lithium hydroxide, monohydrate → HCID 86691265, compound

HRID 2037290Notes

Reaction equation

HRID 2037290 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@:9]1([C:22]([O:24]CC)=[O:23])[CH2:16][C:13]2([CH2:15][CH2:14]2)[C@@H:12]2[C@H:10]1[C@H:11]2[C:17]([O:19]CC)=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+]>O1CCCC1.O>[C:1]([O:5][C:6]([NH:8][C@@:9]1([C:22]([OH:24])=[O:23])[CH2:16][C:13]2([CH2:15][CH2:14]2)[C@@H:12]2[C@H:10]1[C@H:11]2[C:17]([OH:19])=[O:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86691266HCID 86691266, compound

Product 1

HCID 86691265HCID 86691265, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Add diethyl (1S,2S,5R,6S)-2-(tert-butoxycarbonylamino)spiro[bicyclo[3.1.0]hexane-4,1′-cyclopropane]-2,6-dicarboxylate (1.79 g, 4.87 mmol) in tetrahydrofuran (29.2 mL) to a freshly prepared solution of lithium hydroxide monohydrate (1.64 g, 38.97 mmol) in water (19.5 mL) and stir overnight at 60° C. Dilute with water (30 mL), extract with ethyl acetate (2×50 mL). Separate aqueous and organic layers. Wash organic layer with 2M hydrochloric acid. Wash the aqueous layer with 2M hydrochloric acid (25 mL) then extract with ethyl acetate (2×50 mL). Combine the organic layers and wash with brine (15 mL). Dry on magnesium sulfate, filter and concentrate to dryness. Redissolve in dichloromethane and concentrate to dryness to give the title compound (1.49 g, 98%). MS (m/z): 334 (M+23).

Workup

  1. extractionextract with ethyl acetate (2×50 mL)
  2. washWash the aqueous layer with 2M hydrochloric acid (25 mL)
  3. extractionthen extract with ethyl acetate (2×50 mL)
  4. washCombine the organic layers and wash with brine (15 mL)
  5. customDry on magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate to dryness
  8. dissolutionRedissolve in dichloromethane
  9. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-f12f92153672414e84c9317cac2fdaa5
Source dataset
uspto-grants-2013_11
Patent number
US08575214B2

Reaction notes

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