tert-Butanol → 2-Chloro-5-(2,3-dihydroxypropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 1765539노트

반응식

HRID 1765539 반응식
[Cl:1][C:2]1[CH:21]=[CH:20][C:19](CC=C)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[C:25]([OH:29])(C)([CH3:27])[CH3:26].CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:51]C)C=C4)N(CC2)C1.S([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:26][CH:25]([OH:29])[CH2:27][OH:51])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]

참가 물질

7

반응물 4

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 211074042-Chloro-5-(2-propenyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamideHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine

생성물 1

HCID 211074032-Chloro-5-(2,3-dihydroxypropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

시약·촉매·용매 2

HCID 962Water용매2회HCID 8857Ethyl Acetate용매

실험 절차

2-Chloro-5-(2-propenyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (prepared as described in Example 5a) (1.99 g), tert-butanol (40 mL) and water (40 mL) were stirred together under nitrogen and AD-mix-α was added. The mixture was then stirred at room temperature for 20 hours. Sodium sulfite (2 g) was added and the mixture was stirred for 10 minutes. Water (100 mL) and ethyl acetate (100 mL) were then added. The layers were separated and the aqueous layer was further extracted with ethyl acetate (2×100 mL). The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude product. Purification was performed by column chromatography eluting with 5:95 methanol/ethyl acetate to give the sub-titled compound as a solid (1.77 g).

후처리

  1. stirringthe mixture was stirred for 10 minutes
  2. customThe layers were separated
  3. extractionthe aqueous layer was further extracted with ethyl acetate (2×100 mL)
  4. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification
  9. washeluting with 5:95 methanol/ethyl acetate

출처 및 근거

ORD 기록
ord-61eaf422c0c44f159702fbf59b06ac97
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07227038B2

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