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

HRID 576557노트

반응식

HRID 576557 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 ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of compound A (88.2 g, 311 mmol) and DIEA (54.1 mL, 311 mmol) in THF (350 mL) was cooled in an ice bath, followed by the addition of a solution of N-(benzyloxycarbonyl)succinimide (76.6 g, 307 mmol) in THF (150 mL) drop wise over the period of 20 min. The temperature of the reaction mixture was raised to ambient temperature and stirring was continued for an additional 30 min. Solvents were then evaporated and the resulting residue was dissolved in EtOAc (600 mL). The organic layer was extracted with 5% aq. NaHCO3 (2×150 mL) and brine (150 mL). The organic layer was evaporated to provide compound B as yellowish oil. LC-MS [M+H] 305.1 (C13H15F3N2O3+H, calc: 305.3). Compound B was used directly in the next reaction without purification as a MeOH solution.

후처리

  1. customSolvents were then evaporated
  2. dissolutionthe resulting residue was dissolved in EtOAc (600 mL)
  3. extractionThe organic layer was extracted with 5% aq. NaHCO3 (2×150 mL) and brine (150 mL)
  4. customThe organic layer was evaporated

출처 및 근거

ORD 기록
ord-667c560b500547eba3fb5011abfbfb01
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040032B2

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