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HCID 58611852, 화합물 → HCID 10046348, 화합물

HRID 2375216
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HRID 2375216 반응식
C([O:8][NH:9][C:10]([C:12]1[CH:36]=[CH:35][C:15]([O:16][C:17]([C:19]2([C:25]3[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=3)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[O:18])=[CH:14][CH:13]=1)=[O:11])C1C=CC=CC=1>[Pd].CO.C(OCC)C>[OH:8][NH:9][C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:16][C:17]([C:19]2([C:25]3[CH:26]=[CH:27][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:33][CH:34]=3)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)=[O:18])=[CH:35][CH:36]=1)=[O:11]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 1

HCID 58611852HCID 58611852, 화합물

생성물 1

HCID 10046348HCID 10046348, 화합물수율 64.4%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 3283Diethyl Ether용매

실험 절차

A mixture of methyl 4-{1-[(4-{[(benzyloxy)amino]carbonyl}phenoxy)carbonyl] cyclohexyl)-benzoate (E23) (0.063 g, 0.129 mmol) and 5% palladium on activated carbon (0.026 g) in methanol (1 ml) was hydrogenated at room temperature for 50 minutes. The black suspension was filtered, the catalyst was washed with methanol (3×1 ml), and the filtrate was evaporated to give a viscous oil. The oil was converted to white crystals by stirring in diethyl ether (3 ml) overnight. The solid was filtered, washed with diethyl ether (0.5 ml), and dried in vacuum to give the title compound (0.033 g, 64%) as white crystals, m.p. 129-131° C. 1H NMR (DMSO-d6, HMDSO) δ: 1.13-1.99 (8H, m); 2.35-2.58 (2H, m, overlapped with a signal of DMSO); 3.86 (3H, s); 7.05 (2H, d, J=8.6 Hz); 7.65 (2H, d, J=8.4 Hz); 7.77 (2H, d, J=8.6 Hz); 8.01 (2H, d, J=8.4 Hz); 9.07 (1H, s); 11.25 (1H, s). HPLC analysis on Symmetry C8 column: impurities 2.5% (column size 3.9×150 mm; mobile phase acetonitrile−0.1M phosphate buffer (pH 2.5), 60:40; detector UV 254 nm; sample concentration 0.5 mg/ml; flow rate 1.0 ml/min). Anal. Calcd for C22H23NO6*0.35H2O, %: C, 65.45; H, 5.92; N, 3.47. Found, %: C, 65.17; H, 5.76; N, 3.49.

후처리

  1. filtrationThe black suspension was filtered
  2. washthe catalyst was washed with methanol (3×1 ml)
  3. customthe filtrate was evaporated
  4. customto give a viscous oil
  5. filtrationThe solid was filtered
  6. washwashed with diethyl ether (0.5 ml)
  7. customdried in vacuum

출처 및 근거

ORD 기록
ord-546ccc2a479f4353a17b47f4c1f8ddfb
출처 데이터셋
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07465719B2

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