Hydroxylamine → Thiomorpholine-3-carboxamide

HRID 2084946노트

반응식

HRID 2084946 반응식
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]

참가 물질

7

반응물 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

생성물 1

HCID 568316Thiomorpholine-3-carboxamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bba6dce6d8e948b08cfb8dbefe628e67
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06716833B2

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