Diisopropylethylamine → 2-(2-Isopropoxy-3-methyl-benzoylamino)-5-methoxy-indan-2-carboxylic acid ethyl ester

HRID 1047746노트

반응식

HRID 1047746 반응식
[CH:1]([O:4][C:5]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O)([CH3:3])[CH3:2].[CH2:15]([O:17][C:18]([C:20]1([NH2:31])[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:29][CH3:30])[CH:26]=2)[CH2:21]1)=[O:19])[CH3:16].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:15]([O:17][C:18]([C:20]1([NH:31][C:7](=[O:9])[C:6]2[CH:10]=[CH:11][CH:12]=[C:13]([CH3:14])[C:5]=2[O:4][CH:1]([CH3:2])[CH3:3])[CH2:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:29][CH3:30])[CH:26]=2)[CH2:21]1)=[O:19])[CH3:16]

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 593140882-Isopropoxy-3-methyl-benzoic acidHCID 593141282-Amino-5-methoxy-indan-2-carboxylic acid ethyl ester

생성물 1

HCID 593140952-(2-Isopropoxy-3-methyl-benzoylamino)-5-methoxy-indan-2-carboxylic acid ethyl ester수율 90%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2-isopropoxy-3-methyl-benzoic acid (300 mg, 1.54 mmol), 2-amino-5-methoxy-indan-2-carboxylic acid ethyl ester (435 mg, 1.85 mmol), HATU (878 g, 2.31 mmol) in anhydrous DMF (10 mL) is added DIPEA (382 μL, 2.31 mmol). The resulting solution is stirred at RT overnight. After the removal of DMF in vacuo, the residue is dissolved in EtOAc (100 mL) and washed with water (1×10 mL) and brine (2×10 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by flash column chromatography (115 g silica gel, gradient elution: 5%-40% EtOAc in heptane) to give a pure product (92) as a pale yellow oil (569 mg, 90%).

후처리

  1. customAfter the removal of DMF in vacuo
  2. dissolutionthe residue is dissolved in EtOAc (100 mL)
  3. washwashed with water (1×10 mL) and brine (2×10 mL)
  4. dry with materialThe organic layer is dried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash column chromatography (115 g silica gel, gradient elution: 5%-40% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-1c4ee31d5daf41c1b3d03cf169af0083
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569535B2

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