Tetrahydrofuran → Carbamate

HRID 18046

반응식

HRID 18046 반응식
[C:1]([O:5][C:6](=[O:17])[C@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].[C:18](=[O:21])(O)[O-:19].[Na+].C1COCC1.Cl[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30]>C(OCC)C.O>[C:1]([O:5][C:6](=[O:17])[C@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)[NH:8][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])([CH3:4])([CH3:2])[CH3:3].[C:18](=[O:21])([O-:19])[NH2:8]

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 6950582L-Tyrosine 1,1-dimethylethyl ester

생성물 2

HCID 276CarbamateHCID 11428694Z-Tyr-OtBu

시약·촉매·용매 2

HCID 962Water용매HCID 3283Diethyl Ether용매

반응 조건

온도
0 °C

실험 절차

To a 0° C. suspension of L-tyrosine tert-butyl ester (Bachem, 1.0. eq) and sodium bicarbonate (2.0 eq) in a 1:1 mixture of THF and water was added slowly with stirring benzyl chloroformate (1. 1 eq). After the addition, the mixture was stirred at 0° C. for 3 h and at room temperature for 24 h. The mixture was diluted with diethyl ether, and the aqueous layer was separated. The organic extracts were washed with saturated sodium chloride, treated with anhydrous magnesium sulfate, filtered, and evaporated to afford N-benzyloxycarbonyl-L-tyrosine tert-butyl ester of sufficient purity for immediate conversion of the tyrosine hydroxyl into a carbamate.

후처리

  1. additionAfter the addition
  2. customthe aqueous layer was separated
  3. washThe organic extracts were washed with saturated sodium chloride
  4. additiontreated with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-4a6c1f1dc3e74d41b45ee6e37120b17a
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741328B2

연결된 노트

불러오는 중…