Lithium hydroxide, monohydrate → (2S)-2-(((tert-butoxy)carbonyl)amino)hex-5-enoic acid

HRID 2279437Notes

Reaction equation

HRID 2279437 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH2:15][CH:16]=[CH2:17])[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O[Li].O>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH2:15][CH:16]=[CH2:17])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 10444455Boc-L-Homoallylglycine Methyl ester

Product 1

HCID 20765220(2S)-2-(((tert-butoxy)carbonyl)amino)hex-5-enoic acidYield 89.4%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

In a solution of THF/H2O (1:1, 35 mL) containing the product (IX) (1 g, 4.1 mmol) LiOH.H2O (432 mg, 10.3 mmol) is added in one portion. The mixture is stirred for 1 h at room temperature. The solvent is then evaporated and then a 5% H3PO4 solution in water is added until a pH=3 is obtained. The product is then extracted with EtOAc, dried (MgSO4), and then evaporated. After purification, the product (X) (840 mg, 89%) is isolated as a colorless lacquer.

Workup

  1. additionis added in one portion
  2. customThe solvent is then evaporated
  3. additiona 5% H3PO4 solution in water is added until a pH=3
  4. customis obtained
  5. extractionThe product is then extracted with EtOAc
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customAfter purification

Sources & evidence

ORD record
ord-96bc754f3c5746998292374e0b8d2842
Source dataset
uspto-grants-2015_09
Patent number
US09133237B2

Reaction notes

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