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

HRID 2403985노트

반응식

HRID 2403985 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b16db2e93dd04099863ae5cb0110a7db
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802681B2

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