Tetrahydrofuran → N-Cbz-D-serine-2,2,5-trimethylcyclopentyl ester

HRID 35441Notes

Reaction equation

HRID 35441 reaction equation
[C:1]([NH:11][C@@H:12]([C:15]([OH:17])=[O:16])[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1COCC1.[CH3:23][C:24]1([CH3:31])[CH2:28][CH2:27][CH:26]([CH3:29])[CH:25]1O>>[CH3:23][C:24]1([CH3:31])[CH2:28][CH2:27][CH:26]([CH3:29])[CH:25]1[O:16][C:15](=[O:17])[C@@H:12]([CH2:13][OH:14])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 489184Z-D-Ser-OHHCID 212439422,2,5-Trimethylcyclopentanol

Product 1

HCID 22839478N-Cbz-D-serine-2,2,5-trimethylcyclopentyl ester

Procedure

Into a suspension of N-Cbz-D-serine (5 g) in 50 ml of dry THF containing 1 equivalent of 2,2,5-trimethylcyclopentanol is bubbled dry hydrogen chloride gas at room temperature. Upon complete solution of the mixture, the reaction is refluxed for 5 hours, then concentrated. Ethyl acetate is added, and this is washed with saturated sodium bicarbonate, water, and dried over MgSO4. Filtration followed by concentration yields N-Cbz-D-serine-2,2,5-trimethylcyclopentyl ester. 5 g of this product is dissolved in 10 ml methanol and hydrogenated in a Paar apparatus over 1 g of 5% Pd/C to yield 2,2,5-trimethylcyclopentyl-D-serinate.

Workup

  1. customis bubbled dry hydrogen chloride gas at room temperature
  2. temperatureUpon complete solution of the mixture, the reaction is refluxed for 5 hours
  3. concentrationconcentrated
  4. additionEthyl acetate is added
  5. washthis is washed with saturated sodium bicarbonate, water
  6. dry with materialdried over MgSO4
  7. filtrationFiltration
  8. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-316345cd0b0949bea2b08d1244f4febb
Source dataset
uspto-grants-1988_08
Patent number
US04766246

Reaction notes

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