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Triethylamine → (2RS,3S)-3-tert-butyloxycarbonylamino-2-hydroxy-5-methylhexanoic acid

HRID 542371
Notes
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Reaction equation

HRID 542371 reaction equation
[NH2:1][C@@H:2]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]([OH:7])[C:4]([OH:6])=[O:5].C(N(CC)CC)C.[C:19]([O:23][C:24](ON=C(C1C=CC=CC=1)C#N)=[O:25])([CH3:22])([CH3:21])[CH3:20]>O.O1CCOCC1>[C:19]([O:23][C:24]([NH:1][C@@H:2]([CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]([OH:7])[C:4]([OH:6])=[O:5])=[O:25])([CH3:22])([CH3:21])[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 12879199(2RS,3S)-3-amino-2-hydroxy-5-methylhexanoic acid

Product 1

HCID 13848631(2RS,3S)-3-tert-butyloxycarbonylamino-2-hydroxy-5-methylhexanoic acidYield 97.7%

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
2×
HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3.22 g of (2RS, 3S)-3-amino-2-hydroxy-5-methylhexanoic acid and 3.08 ml of triethylamine in 30 ml of water was added a solution of 5.41 g of 2-(tert-butyloxycarbonyloxyimino)-2-phenylacetonitrile in 30 ml of dioxane, and the mixture was stirred ofr 16 hours at room temperature. To the reaction mixture was added 100 ml of water, and the mixture was extracted with ethyl acetate to remove neutral material. The aqueous layer was acidified with an aqueous citric acid solution and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to obtain 5.10 g of (2RS, 3S)-3-tert-butyloxycarbonylamino-2-hydroxy-5-methylhexanoic acid as a pale yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customto remove neutral material
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-51551eb0163c4efca4764b5a557435c0
Source dataset
uspto-grants-1987_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04656269

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes