Lithium hydroxide, monohydrate → Cbz-D-hPro-N(Me)Gly-OH

HRID 1954679Notes

Reaction equation

HRID 1954679 reaction equation
[N:1]1([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:2]1[C:3]([N:5]([CH3:12])[CH2:6][C:7]([O:9]CC)=[O:8])=[O:4].O[Li].O>O1CCOCC1.O>[N:1]1([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:2]1[C:3]([N:5]([CH3:12])[CH2:6][C:7]([OH:9])=[O:8])=[O:4]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 15481639Cbz-D-hPro-N(Me)Gly-OEt

Product 1

HCID 15481640Cbz-D-hPro-N(Me)Gly-OHYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of Cbz-D-hPro-N(Me)Gly-OEt (6 g, 16.6 mmol) in p-dioxane (200 mL) was added a solution of LiOH.H2O (2.78 g, 66.2 mmol) in water (100 mL) with vigorous stirring. After stirring for 12 hours, the solution was concentrated to a volume of 50 mL, diluted with water (100 mL), and extracted twice with diethyl ether (200 mL). The aqueous phase was adjusted to pH 2 with 5N aqueous HCl and extracted three times with ethyl acetate (150 mL). The combined ethyl acetate extracts were dried with MgSO4, filtered, and concentrated to give a white solid (5 g, 91%).

Workup

  1. concentrationthe solution was concentrated to a volume of 50 mL
  2. additiondiluted with water (100 mL)
  3. extractionextracted twice with diethyl ether (200 mL)
  4. extractionextracted three times with ethyl acetate (150 mL)
  5. dry with materialThe combined ethyl acetate extracts were dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d0daa044066e49d2a6a4aa5240be60e4
Source dataset
uspto-grants-2000_09
Patent number
US06124277

Reaction notes

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