Methanamine, N-methoxy-, hydrochloride (1:1) → 3-Furancarboxamide,tetrahydro-N-methoxy-N-methyl-(9CI)

HRID 588407ノート

反応式

HRID 588407 の反応式
[O:1]1[CH2:5][CH2:4][CH:3]([C:6]([OH:8])=O)[CH2:2]1.CN([C:12]([O:16][N:17]1N=NC2C=CC=C[C:18]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CNOC.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:12][O:16][N:17]([CH3:18])[C:6]([CH:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[O:8]

参加物

6

反応物 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 4661317(R)-Tetrahydro-3-furoic acid

生成物 1

HCID 450845223-Furancarboxamide,tetrahydro-N-methoxy-N-methyl-(9CI)収率 161.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Tetrahydro-3-furoic acid (412 μL, 4.31 mmol) was dissolved in DMF (18 mL) and HBTU (1.96 g, 5.17 mmol) was added. The reaction mixture was stirred for 1 h and N,O-dimethylhydroxylamine hydrochloride (504 mg, 5.17 mmol) and DIPEA (2.25 mL, 12.9 mmol) were added. The reaction mixture was stirred overnight and concentrated in vacuo. The residue was diluted with DCM (40 mL) and washed with sat aq NH4Cl (20 mL) and sat aq Na2CO3 (20 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by normal phase column chromatography to give the crude title compound as a yellow gum (1.11 g). LCMS (ES+): 160.1 (M+H)+.

後処理

  1. stirringThe reaction mixture was stirred overnight
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with DCM (40 mL)
  4. washwashed
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by normal phase column chromatography

出典と根拠

ORDレコード
ord-93b3c29396b54e698ae151c0a73edf7e
出典データセット
uspto-grants-2016_01
特許番号
US09227967B2

反応ノート

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