Morpholine → HCID 57386559, 화합물

HRID 420265노트

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HRID 420265 반응식
C(OC([C:7]1([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[C:25]([F:32])[CH:24]=2)[C:12](=[O:13])[CH:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][S:9][CH2:8]1)=O)C=C.N1CCOCC1.C([O-])(O)=O.[Na+]>C1COCC1>[C:18]([O:17][C:15](=[O:16])[NH:14][C@@H:11]1[C:12](=[O:13])[C@H:7]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[C:25]([F:32])[CH:24]=2)[CH2:8][S:9][CH2:10]1)([CH3:21])([CH3:19])[CH3:20]

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 666496345-tert-Butoxycarbonylamino-3-(3-fluoro-4-nitro-benzyl)-4-oxo-tetrahydro-thiopyran-3-carboxylic acid allyl ester

생성물 1

HCID 57386559HCID 57386559, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
25 °C

실험 절차

To a degassed solution of 5-tert-butoxycarbonylamino-3-(3-fluoro-4-nitro-benzyl)-4-oxo-tetra-hydro-thiopyran-3-carboxylic acid allyl ester (3.56 g, 7.6 mmol) and morpholine (1.4 mL, 15.2 mmol) in THF (50 mL) was added under argon Pd(PPh3)4 (0.092 g, 0.076 mmol) and the reaction mixture was stirred at 25° C. for 3 h. The reaction mixture was poured onto cold saturated NaHCO3 solution and extracted with EtOAc. Combined extracts were washed with brine, dried over MgSO4 and evaporated. The residue was re-dissolved in THF (10 mL) and kept at 25° C. for 3 h after addition of a catalytic amount of DBU. The title compound was obtained after evaporation and crystallization from diisopropylether as single diastereoisomer: TLC (hexane-EtOAc 1:2) Rf=0.38; HPLC RtA=2.17 min; ESIMS [M+NH4]+=402; 1H NMR (400 MHz, CDCl3): δ 8.0 (dd, 1H), 7.14 (m, 2H), 5.68 (m, 1H), 4.54 (m, 1H), 3.41 (m, 1H), 3.28 (dd, 1H), 3.14 (m, 1H), 2.84 (ddd, 1H), 2.69 (dd, 1H), 2.65 (m, 2H), 1.42 (s, 9H).

후처리

  1. extractionextracted with EtOAc
  2. washCombined extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. dissolutionThe residue was re-dissolved in THF (10 mL)
  6. waitkept at 25° C. for 3 h
  7. additionafter addition of a catalytic amount of DBU

출처 및 근거

ORD 기록
ord-acb3784f7b874f808f7a13895c6ec269
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093406B2

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