Cesium carbonate → 3-(Tert-butoxycarbonylamino-methyl)-5-methyl-hexanoic acid 1-isobutyryloxy-ethyl ester

HRID 1361046노트

반응식

HRID 1361046 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].C(O[C:10]([O:12][CH:13]([O:15][C:16](=[O:32])[CH2:17][CH:18]([CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH3:14])=[O:11])C.IC(O[C:37](=O)[CH:38](C)[CH3:39])C>CO.CC#N>[C:10]([O:12][CH:13]([O:15][C:16](=[O:32])[CH2:17][CH:18]([CH2:23][NH:24][C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH2:19][CH:20]([CH3:21])[CH3:22])[CH3:14])(=[O:11])[CH:38]([CH3:39])[CH3:37]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 14633820Propanoic acid, 2-methyl-, 1-iodoethyl esterHCID 723692293-(Tert-butoxycarbonylamino-methyl)-5-methyl-hexanoic acid 1-ethyloxycarbonyloxy-ethyl ester

생성물 1

HCID 723692273-(Tert-butoxycarbonylamino-methyl)-5-methyl-hexanoic acid 1-isobutyryloxy-ethyl ester수율 27.2%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6342Acetonitrile용매2회

실험 절차

Cesium carbonate (0.365 g, 1.12 mmol) was dissolved in methanol (5 mL) and S-form of compound 4 (0.500 g, 1.28 mmol) was added. The solution was stirred for 4 hours at room temperature and concentrated to dryness. The residue was diluted with CH3CN (7.5 mL), and compound 14 (0.945 g, 3.56 mmol) and CH3CN (5 mL) were then added. After stirring overnight at room temperature, the reaction solution was filtered and concentrated to give 1 g of the crude product, which was then purified by chromatography on a column of silica gel (70-230 mesh, elution: EA/Hexane=1:4). Compound 3-(tert-butoxycarbonylamino-methyl)-5-methyl-hexanoic acid 1-isobutyryloxy-ethyl ester 15 (0.13 g) was obtained with 27% yield. 1HNMR (CDCl3, 500 MHz) δ0.87-0.92 (m, 6H), 1.10-1.21 (m, 2H), 1.55 (d, J=5 Hz, 6H), 1.44 (s, 9H), 1.48 (d, J=5.5 Hz, 3H), 1.52-1.59 (m, 2H), 2.06-2.12 (m, 1H), 2.28-2.35 (m, 2H), 2.49-2.57 (m, 1H), 2.93-3.06 (m, 1H), 3.12-3.22 (m, 1H), 4.62-4.73 (m, 1H), 6.84 (q, J=5.5 Hz, 1H).

후처리

  1. concentrationconcentrated to dryness
  2. additionwere then added
  3. stirringAfter stirring overnight at room temperature
  4. filtrationthe reaction solution was filtered
  5. concentrationconcentrated
  6. customto give 1 g of the crude product, which
  7. customwas then purified by chromatography on a column of silica gel (70-230 mesh, elution: EA/Hexane=1:4)

출처 및 근거

ORD 기록
ord-e32920b6c0f040e7900d315776f2d569
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879906B2

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