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

HRID 927911ノート

反応式

HRID 927911 の反応式
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

参加物

4

反応物 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-carboxylate2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d613f285db3f48fb8730553d3f1e1bb4
出典データセット
uspto-grants-2016_03
特許番号
US09290472B2

反応ノート

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