Trifluoroacetic acid → methyl cis-(3aRS,9bRS)-7-amino-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylate

HRID 927911노트

반응식

HRID 927911 반응식
FC(F)(F)C(O)=O.C(OC([N:15](C(OC(C)(C)C)=O)[C:16]1[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]2[C:19]([C@H:20]3[CH2:32][CH2:31][O:30][C@H:21]3[CH2:22][O:23]2)=[CH:18][CH:17]=1)=O)(C)(C)C>C(Cl)Cl>[NH2:15][C:16]1[C:25]([C:26]([O:28][CH3:29])=[O:27])=[C:24]2[C:19]([C@H:20]3[CH2:32][CH2:31][O:30][C@H:21]3[CH2:22][O:23]2)=[CH:18][CH:17]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86713278methyl cis-(3aRS,9bRS)-7-[bis-(tert-butoxycarbonyl)amino]-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylate2회

생성물 1

HCID 86713281methyl cis-(3aRS,9bRS)-7-amino-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylate수율 69.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid (7 mL) was added to a solution of methyl cis-(3aRS,9bRS)-7-[bis-(tert-butoxycarbonyl)amino]-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylate (Intermediate 2, 0.66 g) in DCM (15 mL) and the mixture was stirred at room temperature for 1 hour. The mixture was evaporated to dryness and the residue was treated with aqueous sodium bicarbonate and extracted with DCM, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give methyl cis-(3aRS,9bRS)-7-amino-1,3a,4,9b-tetrahydro-2H-furo[2,3-c]chromene-6-carboxylate (0.255 g) as a gum.

후처리

  1. customThe mixture was evaporated to dryness
  2. additionthe residue was treated with aqueous sodium bicarbonate
  3. extractionextracted with DCM
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

출처 및 근거

ORD 기록
ord-d613f285db3f48fb8730553d3f1e1bb4
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

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