Tetrahydrofuran → Carbamate

HRID 18046

反応式

HRID 18046 の反応式
[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]

参加物

8

反応物 4

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

生成物 2

HCID 276CarbamateHCID 11428694Z-Tyr-OtBu

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4a6c1f1dc3e74d41b45ee6e37120b17a
出典データセット
uspto-grants-2010_06
特許番号
US07741328B2

関連ノート

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