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Sodium Hydroxide → methyl (1aRS,7bSR)-5-(2-carboxymethyl-4-fluorobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate

HRID 927968
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HRID 927968 반응식
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]3[C:17]([CH:18]4[CH2:28][CH:19]4[CH2:20][O:21]3)=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[C:6]([CH2:29][C:30]([O:32]C)=[O:31])[CH:5]=1>CO>[C:30]([CH2:29][C:6]1[CH:5]=[C:4]([F:3])[CH:9]=[CH:8][C:7]=1[S:10]([NH:13][C:14]1[C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]2[C:17]([CH:18]3[CH2:28][CH:19]3[CH2:20][O:21]2)=[CH:16][CH:15]=1)(=[O:12])=[O:11])([OH:32])=[O:31]
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참가 물질

4

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HCID 14798Sodium HydroxideHCID 71006868methyl (1aRS,7bSR)-5-[4-fluoro-2-(methoxycarbonylmethyl)-benzenesulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate2회

생성물 1

HCID 71006995methyl (1aRS,7bSR)-5-(2-carboxymethyl-4-fluorobenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate수율 99.5%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
50 °C

실험 절차

1M Sodium hydroxide solution (3 mL) was added to a solution of methyl (1aRS,7bSR)-5-(4-fluoro-2-methoxycarbonylmethylbenzenesulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa-[c]chromene-4-carboxylate (Intermediate 84, 0.438 g) in methanol (6 mL) and the mixture was heated at 50° C. for 2 hours. After cooling, the mixture was evaporated to dryness and the residue was dissolved in ethyl acetate and water and acidified with concentrated hydrochloric acid. The organic layer was dried (Na2SO4) and filtered and the filtrate was concentrated in vacuo, the residue was dissolved in toluene and re-evaporated to give methyl (1aRS,7bSR)-5-(2-carboxymethyl-4-fluorobenzene-sulfonylamino)-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate (0.422 g) as a white solid.

후처리

  1. temperatureAfter cooling
  2. customthe mixture was evaporated to dryness
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. dissolutionthe residue was dissolved in toluene
  8. customre-evaporated

출처 및 근거

ORD 기록
ord-59bd4f2f1aba430389ca9606604574c3
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09290472B2

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