1,2-Dichloroethane → (e)-3-{1'-Tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-n-(tetrahydro-pyran-2-yloxy)-acrylamide

HRID 2046711

반응식

HRID 2046711 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:22][C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[C:18](/[CH:24]=[CH:25]/[C:26](O)=[O:27])[CH:19]=3)[O:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:43][O:44][CH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][O:46]1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([CH2:22][C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[C:18](/[CH:24]=[CH:25]/[C:26]([NH:43][O:44][CH:45]4[CH2:50][CH2:49][CH2:48][CH2:47][O:46]4)=[O:27])[CH:19]=3)[O:14]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 52952089(E)-3-{1'-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-acrylic acid

생성물 1

HCID 87208986(e)-3-{1'-Tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4'-piperidine]-6-yl}-n-(tetrahydro-pyran-2-yloxy)-acrylamide수율 95.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of (E)-3-{1′-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-acrylic acid (387 mg, 1 mmol) in DCM (15 ml) was cooled down to 0° C. EDC (383 mg, 2 mmol) and HOBT (135 mg, 1 mmol) were added, and the mixture was stirred at RT for 1 h. NH2OTHP (146 mg, 1.25 mmol) in DCM (1 ml) was added dropwise and the mixture was stirred at RT. After 4 h, the reaction mixture was washed with a saturated NaHCO3 solution and brine, dried over Na2SO4 and concentrated. The crude residue was purified by column chromatography (eluent:DCM/MeOH 98:2) to give (E)-3-{1′-tert-butoxycarbonyl-4-oxo-spiro[chromane-2,4′-piperidine]-6-yl}-N-(tetrahydro-pyran-2-yloxy)-acrylamide (464 mg) as a light yellow oil.

후처리

  1. stirringthe mixture was stirred at RT
  2. waitAfter 4 h
  3. washthe reaction mixture was washed with a saturated NaHCO3 solution and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude residue was purified by column chromatography (eluent:DCM/MeOH 98:2)

출처 및 근거

ORD 기록
ord-81c3561a72724c01aeff9f0065f528a5
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592444B2

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