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Phenylethanolamine → tert-butyl N-(2-hydroxy-2-phenylethyl)carbamate

HRID 256009
ノート
印刷プレビュー

反応式

HRID 256009 の反応式
[C:1]([O:5][C:6]([N:8]=[N+]=[N-])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.[CH:14]1[CH:19]=[CH:18][C:17]([CH:20]([OH:23])[CH2:21]N)=[CH:16][CH:15]=1>C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][CH2:21][CH:20]([C:17]1[CH:18]=[CH:19][CH:14]=[CH:15][CH:16]=1)[OH:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1000PhenylethanolamineHCID 6344DichloromethaneHCID 61256Carbonazidic acid, 1,1-dimethylethyl ester

生成物 1

HCID 9816137tert-butyl N-(2-hydroxy-2-phenylethyl)carbamate

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

28 g of t-butoxycarbonyl azide were added at room temperature to 200 ml of a methylene chloride solution containing 25.3 g of DL-2-amino-1-phenylethanol and 45 ml of triethylamine, and the reaction mixture was allowed to stand overnight at room temperature. The reaction mixture was then condensed by evaporation under reduced pressure, and water and diisopropyl ether were added to the condensate. The mixture was thoroughly stirred. yielding the title compound in the form of insoluble crystals melting at 123°-124° C. in a yield of 20.6 g. These crystals were filtered off. The organic layer in the filtrate was separated and washed with an aqueous solution of potassium hydrogen sulfate and with an aqueous solution of sodium bicarbonate. The resulting solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The crystals of the title compound in the residue were collected by filtration and washed with a mixture of diisopropyl ether and petroleum ether, yielding a further 18.7 g.

後処理

  1. customcondensed
  2. customby evaporation under reduced pressure, and water and diisopropyl ether
  3. additionwere added to the condensate

出典と根拠

ORDレコード
ord-feb10c0b70ae4a0ba5c306591363acd7
出典データセット
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04699905

反応ノート

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