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

HRID 2232689ノート

反応式

HRID 2232689 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-534ac3e1eb594089be47259796c39af6
出典データセット
uspto-grants-1988_11
特許番号
US04788332

反応ノート

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