Diisopropylethylamine → 2-[(2,3-Dihydrobenzofuran-2-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester

HRID 1047821

反応式

HRID 1047821 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1[C:10]([OH:12])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:46]([O:48][C:49]([C:51]1([NH2:60])[CH2:59][C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[CH2:52]1)=[O:50])[CH3:47]>CO.C(Cl)Cl.C(Cl)Cl>[CH2:46]([O:48][C:49]([C:51]1([NH:60][C:10]([CH:2]2[CH2:3][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[O:1]2)=[O:12])[CH2:59][C:58]2[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=2)[CH2:52]1)=[O:50])[CH3:47]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27765552,3-Dihydro-1-benzofuran-2-carboxylic acidHCID 10921653Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate

生成物 1

HCID 593141982-[(2,3-Dihydrobenzofuran-2-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester収率 171.4%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21226129Dichloromethane methanol溶媒

実験手順

To a 40 mL vial containing a stirring bar, 2,3-dihydro-1-benzofuran-2-carboxylic acid (0.4 g, 2.44 mmol) is charged with dry DCM (7 mL). Stirring is initiated. HBTU (922 mg, 2.43 mmol) and the DIPEA (0.95 mL, 8.0 mmol) are added. The 2-aminoindane-2-carboxylic acid ethyl ester (500 mg, 2.44 mmol) is added. The reaction is allowed to stir for 16 h. Analysis by tlc of the reaction mixture (silica, 10% MeOH/DCM) indicates complete consumption of the starting amine. The contents of the reaction flask are diluted with EtOAc (50 mL) and transferred to a separatory funnel. This is washed consecutively with dilute aqueous NaHCO3 (25 mL) and brine (25 mL), dried over MgSO4, filtered and evaporated in vacuo to provide 1.47 g of viscous yellow oil. This material is dissolved in 10 mL of DCM and purified utilizing an ISCO Companion with a 40 g cartridge of silica. The gradient is 15% EtOAc in heptanes for 3 column volumes followed by a linear gradient to 50% over 8 column volumes and then 90% EtOAc for 2 column volumes with a ramp of 1 column volume. 25 mL fractions are collected. Fractions 3 through 6 are combined and evaporated in vacuo. Pumping to a constant weight gives amorphous white solid 0.68 g.

後処理

  1. additionTo a 40 mL vial containing a stirring bar
  2. stirringto stir for 16 h
  3. customconsumption of the starting amine
  4. additionThe contents of the reaction flask are diluted with EtOAc (50 mL)
  5. customtransferred to a separatory funnel
  6. washThis is washed consecutively with dilute aqueous NaHCO3 (25 mL) and brine (25 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo

出典と根拠

ORDレコード
ord-f49a726123554ba09691b993d986299c
出典データセット
uspto-grants-2013_10
特許番号
US08569535B2

関連ノート

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