Lithium hydroxide, monohydrate → HCID 68311093, compound

HRID 633847Notes

Reaction equation

HRID 633847 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:22])[CH2:7][C@@H:8]1[CH2:13][CH2:12][C@@H:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][O:9]1>CO.O>[C:18]([O:17][C:15]([NH:14][C@H:11]1[CH2:10][O:9][C@H:8]([CH2:7][C:6]([OH:22])=[O:5])[CH2:13][CH2:12]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86730721HCID 86730721, compound

Product 1

HCID 68311093HCID 68311093, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide monohydrate (61 mg, 1.46 mmol, 2.0 eq) is added at room temperature to a stirred solution of (2S,5R)-(5-tert-butoxycarbonylamino-tetrahydro-pyran-2-yl)-acetic acid methyl ester (200 mg, 0.73 mmol, 1.0 eq) in methanol (10 mL) and water (5 mL) and the resulting mixture is stirred at room temperature for 2 hours. Then solvents are evaporated, the residue is acidified to pH 2 with 2.0 M hydrochloric acid aqueous solution and the resulting aqueous layer is extracted with ethyl acetate (3×20 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford (2S,5R)-(5-tert-butoxycarbonylamino-tetrahydro-pyran-2-yl)-acetic acid as a colorless oil (150 mg, 79% yield).

Workup

  1. customThen solvents are evaporated
  2. extractionthe resulting aqueous layer is extracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5ee76d56c84341e78da1aea72b7837de
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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