Hydroxylamine → Thiomorpholine-3-carboxamide

HRID 2084946ノート

反応式

HRID 2084946 の反応式
C[C:2]1(C)[S:7][CH2:6][CH2:5][N:4](S(C2C=CC(OCC#CCCOC3CCCCO3)=CC=2)(=O)=O)[CH:3]1[C:30]([OH:32])=O.O[N:35]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.NO>CN(C=O)C.C(OCC)(=O)C>[NH:4]1[CH2:5][CH2:6][S:7][CH2:2][CH:3]1[C:30]([NH2:35])=[O:32]

参加物

7

反応物 4

HCID 787HydroxylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 226449072,2-dimethyl-4-[(4-{[5-(tetrahydro-2H-pyran-2-yloxy)2-pentynyl]oxy}phenyl)sulfonyl]-3-thiomorpholine carboxylic acid

生成物 1

HCID 568316Thiomorpholine-3-carboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 0.28 g (0.56 mmol) of 2,2-dimethyl-4-[(4-{[5-(tetrahydro-2H-pyran-2-yloxy)-2-pentynyl]oxy}phenyl)sulfonyl]-3-thiomorpholine carboxylic acid and 0.091 g (0.675 mmol) of 1-hydroxybenzotriazole in 2.5 mL of DMF was added 0.151 g (0.788 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and stirred at room temperature for 1 h. Then 0.173 mL (2.8 mmol) of 50% aqueous hydroxylamine was added and the reaction was stirred for 18 h. The resulting mixture was diluted with ethyl acetate, washed with water, brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 5% methanol/dichloromethane. The product was triturated with ether to provide 0.024 g (8%) of N-hydroxy-2,2-dimethyl-4-[(4-{[5-tetrahydro-2H-pyran-2-yloxy)-2-pentynyl]oxy}phenyl)sulfonyl]-3-thiomorpholine carboxamide as a white solid.

後処理

  1. stirringthe reaction was stirred for 18 h
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with 5% methanol/dichloromethane
  7. customThe product was triturated with ether

出典と根拠

ORDレコード
ord-bba6dce6d8e948b08cfb8dbefe628e67
出典データセット
uspto-grants-2004_04
特許番号
US06716833B2

反応ノート

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