Morpholine → Methyl 2-hydroxy-5-(4-morpholinylcarbonyl)benzoate

HRID 1623727노트

반응식

HRID 1623727 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].C(N(C(C)C)CC)(C)C.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.O.C(OCC)(=O)C.C(Cl)CCl>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:8])=[CH:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12]

참가 물질

9

반응물 4

HCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 132228014-Hydroxy-3-(methoxycarbonyl)benzoic acid

생성물 1

HCID 67107453Methyl 2-hydroxy-5-(4-morpholinylcarbonyl)benzoate

시약·촉매·용매 4

HCID 111,2-Dichloroethane용매2회HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4-hydroxy-3-[(methyloxy)carbonyl]benzoic acid (may be prepared as described in Description 107, 1.31 g, 6.68 mmol) in N,N-dimethylformamide (10 ml) was added diisopropylethylamine (2.33 ml, 13.36 mmol), morpholine (1.75 ml, 20.03 mmol), HOBT (1.33 g, 8.68 mmol) and EDC (2.56 g, 13.36 mmol). The solution was stirred at room temperature for 18 hours then another equivalent of EDC was added (1.28 g, 13.38 mmol). The solution was stirred for another 6 hours then ethyl acetate (20 ml) and water were added. The organic layer was separated, washed with water (3×10 ml), dried (MgSO4) and the solvent removed in vacuo to give a gum. Purification by MDAP yielded the title compound as a gum. 560 mg.

후처리

  1. stirringThe solution was stirred for another 6 hours
  2. customThe organic layer was separated
  3. washwashed with water (3×10 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give a gum
  7. customPurification by MDAP

출처 및 근거

ORD 기록
ord-1c86fd1c1a474945b3174b2d16980957
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778939B2

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