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

HRID 1623727ノート

反応式

HRID 1623727 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 111,2-Dichloroethane溶媒2 回HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1c86fd1c1a474945b3174b2d16980957
出典データセット
uspto-grants-2014_07
特許番号
US08778939B2

反応ノート

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