Diisopropylethylamine → Methyl-[2-(2,2,2-trifluoro-acetylamino)-ethyl]carbamic acid benzyl ester

HRID 2403985ノート

反応式

HRID 2403985 の反応式
[F:1][C:2]([F:11])([F:10])[C:3]([NH:5]CCNC)=[O:4].CCN(C(C)C)C(C)C.[CH2:21]([O:28][C:29]([N:31]1[C:35](=O)[CH2:34]C[C:32]1=O)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([O:28][C:29](=[O:30])[N:31]([CH3:32])[CH2:35][CH2:34][NH:5][C:3](=[O:4])[C:2]([F:11])([F:10])[F:1])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 3826287Benzyl 2,5-dioxopyrrolidine-1-carboxylateHCID 107022842,2,2-trifluoro-N-[2-(methylamino)ethyl]acetamide

生成物 1

HCID 58480374Methyl-[2-(2,2,2-trifluoro-acetylamino)-ethyl]carbamic acid benzyl ester収率 101%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of compound A (96.8 g, 340.7 mmol) and DIEA (59.3 ml, 340.7 mmol) in THF (350 ml) was cooled to ˜5° C., followed by addition of a solution of N-(benzyloxycarbonyl)succinimide (84.0 g, 337.3 mmol) in THF (150 ml) dropwise over the period of 20 min The temperature of reaction mixture was raised to room temperature and stirring was continued for an additional 30 min, followed by the solvents being evaporated. The resultant residue was dissolved in EtOAc (600 ml). EtOAc was extracted with 5% aq. NaHCO3 (2×150 ml) and brine (150 ml). The organic layer was separated and evaporated to provide compound B as yellowish oil (103.0 g, 340.7 mmol). LC-MS [M+H] 305.3 (C13H15F3N2O3+H, calc: 305.3). Compound B was used without further purification.

後処理

  1. customThe temperature of reaction mixture
  2. custombeing evaporated
  3. dissolutionThe resultant residue was dissolved in EtOAc (600 ml)
  4. extractionEtOAc was extracted with 5% aq. NaHCO3 (2×150 ml) and brine (150 ml)
  5. customThe organic layer was separated
  6. customevaporated

出典と根拠

ORDレコード
ord-b16db2e93dd04099863ae5cb0110a7db
出典データセット
uspto-grants-2014_08
特許番号
US08802681B2

反応ノート

読み込み中…