Lithium hydroxide, monohydrate → HCID 178454076, compound

HRID 1257700Notes

Reaction equation

HRID 1257700 reaction equation
C([O:3][C:4](=[O:21])[CH2:5][O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9][CH2:8]1)C.O.[OH-].[Li+]>CO.O>[C:17]([O:16][C:14]([NH:13][C@H:10]1[CH2:11][CH2:12][C@H:7]([O:6][CH2:5][C:4]([OH:21])=[O:3])[CH2:8][CH2:9]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178473104HCID 178473104, compound

Product 1

HCID 178454076HCID 178454076, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of trans (4-tert-butoxycarbonylamino-cyclohexyloxy)-acetic acid ethyl ester (720 mg, 2.40 mmol) in methanol (18 mL) and water (6 mL) as treated with lithium hydroxide monohydrate (210 mg, 5.00 mmol) and stirred at ambient temperature for 2.25 hours. Methanol was removed under vacuum and the residue partitioned between ethyl acetate and 1M HCl. The phases were separated and the aqueous phase extracted into ethyl acetate (2×). The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated under vacuum to afford 600 mg (92%) of trans (4-tert-butoxycarbonylamino-cyclohexyloxy)-acetic acid as a white solid. LCMS (Method Q, ESI): RT=2.96 min, m+H=296.0; 1H NMR (400 MHz, CDCl3) δ: 4.38 (br s, 1H), 4.12 (s, 2H), 3.41 (m, 2H), 2.04 (m, 4H), 1.44 (m, 11H), 1.15 (m, 2H).

Workup

  1. customMethanol was removed under vacuum
  2. customthe residue partitioned between ethyl acetate and 1M HCl
  3. customThe phases were separated
  4. extractionthe aqueous phase extracted into ethyl acetate (2×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-340e3df7ac3e4e769c24e6738706a2d4
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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