(+)-8-Phenylmenthol → (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 5-(3-bromo-4-fluorophenyl)-4,6-dioxo-1,3,4,5,6,7,8,9-octahydro-2H-cyclopenta[b][1,7]naphthyridine-2-carboxylate

HRID 478262

반응식

HRID 478262 반응식
C([N:8]1[CH2:17][C:16]2[NH:15][C:14]3[CH2:18][CH2:19][C:20](=[O:21])[C:13]=3[CH:12]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([Br:29])[CH:23]=3)[C:11]=2[C:10](=[O:30])[CH2:9]1)C1C=CC=CC=1.Cl[C:32]([O:34][CH:35]1[CH:40]([C:41]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([CH3:43])[CH3:42])[CH2:39][CH2:38][CH:37]([CH3:50])[CH2:36]1)=[O:33].C1(C(C)(C)C2CCC(C)CC2O)C=CC=CC=1>C1COCC1>[Br:29][C:24]1[CH:23]=[C:22]([CH:12]2[C:11]3[C:10](=[O:30])[CH2:9][N:8]([C:32]([O:34][C@@H:35]4[CH2:36][C@H:37]([CH3:50])[CH2:38][CH2:39][C@H:40]4[C:41]([CH3:42])([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)[CH3:43])=[O:33])[CH2:17][C:16]=3[NH:15][C:14]3[CH2:18][CH2:19][C:20](=[O:21])[C:13]2=3)[CH:27]=[CH:26][C:25]=1[F:28]

참가 물질

5

반응물 3

HCID 577105(+)-8-PhenylmentholHCID 113288132-benzyl-5-(3-bromo-4-fluorophenyl)-2,3,5,7,8,9-hexahydro-1H-cyclopenta[b][1,7]naphthyridine-4,6-dioneHCID 145714908-Phenylmenthol chloroformate

생성물 1

HCID 69302932(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 5-(3-bromo-4-fluorophenyl)-4,6-dioxo-1,3,4,5,6,7,8,9-octahydro-2H-cyclopenta[b][1,7]naphthyridine-2-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of the product from Example 5A (1.9 g, 4.0 mmol) in THF (30 mL) was treated with 8-phenylmenthol chloroformate prepared from (−)-8-phenylmenthol as described in (Yamamoto, Y., J.Amer.Chem.Soc. (1992), 114, 121-125) (1.45 g, 4.92 mmol) in THF (10 mL), stirred for 3 days at ambient temperature and partitioned between aqueous sodium bicarbonate and methylene chloride. The organic layer was separated, dried with sodium sulfate, filtered and concentrated to provide a mixture of diastereomeric carbamates. The diastereomeric mixture was subjected to column chromatography over silica gel (20% hexanes/ethyl acetate) to provide the title compound (0.32 g) as the less polar diastereomer and mixed fractions containing both diastereomers (0.9 g).

후처리

  1. custompartitioned between aqueous sodium bicarbonate and methylene chloride
  2. customThe organic layer was separated
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide

출처 및 근거

ORD 기록
ord-5f9475acc7f94d3db67c4a8fcfa590fe
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642222B2

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