Hydrochloric Acid → HCID 11609154, 화합물

HRID 2378370노트

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HRID 2378370 반응식
C[O:2][C:3](=[O:23])[CH2:4][CH2:5][C:6]1([CH3:22])[CH2:15][CH2:14][C:13]2[C:8](=[C:9]3[CH:20]4[CH2:21][CH:17]([CH2:18][CH2:19]4)[C:10]3=[C:11]([OH:16])[CH:12]=2)[O:7]1.[OH-].[Na+].O1CCOCC1.Cl>C(OCC)(=O)C.O>[OH:16][C:11]1[CH:12]=[C:13]2[C:8](=[C:9]3[CH:20]4[CH2:21][CH:17]([CH2:18][CH2:19]4)[C:10]=13)[O:7][C:6]([CH2:5][CH2:4][C:3]([OH:23])=[O:2])([CH3:22])[CH2:15][CH2:14]2

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 11716671HCID 11716671, 화합물

생성물 1

HCID 11609154HCID 11609154, 화합물수율 73.3%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

1.0 gram (3.16 mmol) of 3-(6-hydroxy-2-methyl-3,4,7,8,9,10-hexahydro-7,10-methano-2H-benzo[h]chromen-2-yl)-propionic acid methyl ester, prepared as described in Example 13, was mixed with 20 mL of 2N NaOH and 20 mL of dioxane, the mixture was stirred for 5 hours and was acidified with dilute HCl. Water and ethyl acetate were added and the organic layer was separated, washed and dried over MgSO4. After the removal of solvents, the residue was further purified by flash column chromatography on silica gel (3:2 ethyl acetate/hexane) to afford 700 mg of 3-(6-hydroxy-2-methyl-3,4,7,8,9,10-hexahydro-7,10-methano-2H-benzo[h]chromen-2-yl)-propionic acid. 1H-NMR (300 MHz, CDCl3) δ (ppm): 6.29 (s, 1H), 4.70 (s, 1H), 3.52-3.46 (d, 2H), 2.69-2.55 (m, 2H), 2.52-2.47 (m, 2H), 2.00-1.64 (m, 8H), 1.43-1.15 (m,5H); MS: 302 (M+H+, 73%), 325 (M+Na+, 100%).

후처리

  1. customthe organic layer was separated
  2. washwashed
  3. dry with materialdried over MgSO4
  4. customAfter the removal of solvents
  5. customthe residue was further purified by flash column chromatography on silica gel (3:2 ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-e4370981241248a5929cb401da5b73e7
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07470798B2

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