Sodium Hydroxide → ((2R,3R)-3-benzyloxy-2-t-butoxycarbonylaminobutoxy)acetic acid

HRID 1677061Notes

Reaction equation

HRID 1677061 reaction equation
[OH-:1].[Na+].[C:3]([O:7][C:8]([N:10]1[C:15](=[O:16])[CH2:14][O:13][CH2:12][C@@H:11]1[C@H:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:18])=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO>[CH2:20]([O:19][C@H:17]([CH3:18])[C@H:11]([NH:10][C:8]([O:7][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:9])[CH2:12][O:13][CH2:14][C:15]([OH:1])=[O:16])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67373558HCID 67373558, compound

Product 1

HCID 67373378((2R,3R)-3-benzyloxy-2-t-butoxycarbonylaminobutoxy)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2 N sodium hydroxide solution (250 mL) was added to a methanol (250 mL) solution of (R)-3-((R)-1-benzyloxyethyl)-5-oxomorpholine-4-carboxylic acid t-butyl ester (40 g), and stirring was continued for 3 hours at room temperature. The methanol was removed under a vacuum, and ether was added, and the aqueous layer was partitioned. The aqueous layer was washed with ether, and the pH was adjusted to approximately pH 4 with a 5% citric acid solution. The resultant was extracted twice with ethyl acetate and washed twice with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under a vacuum, and the title compound (42.1 g) was obtained. The physical property values are as follows.

Workup

  1. customThe methanol was removed under a vacuum, and ether
  2. additionwas added
  3. customthe aqueous layer was partitioned
  4. washThe aqueous layer was washed with ether
  5. extractionThe resultant was extracted twice with ethyl acetate
  6. washwashed twice with water
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customthe solvent was removed under a vacuum

Sources & evidence

ORD record
ord-52f491b838e4405aa85a20f2302c8cbc
Source dataset
uspto-grants-2011_08
Patent number
US08008293B2

Reaction notes

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