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

HRID 1722905
Notes
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Reaction equation

HRID 1722905 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 for 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 materials. The aqueous layer was acidified by the addition of an aqueous citric acid solution, and the acid solution was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated 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 materials
  3. additionThe aqueous layer was acidified by the addition of an aqueous citric acid solution
  4. extractionthe acid solution was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c128414d6a804fed8f8b04332b070d63
Source dataset
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04857650

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes