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Trifluoroacetic acid → 2-Amino-1-[4-cyclopentyl-6-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-3,3-dimethyl-butan-1-one

HRID 1949626
ノート
印刷プレビュー

反応式

HRID 1949626 の反応式
C(OC(=O)[NH:7][CH:8]([C:13]([N:15]1[CH2:19][CH2:18][CH:17]2[N:20]([CH:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[CH2:21][CH:22]([C:23]3[C:31]4[C:26](=[CH:27][C:28]([F:32])=[CH:29][CH:30]=4)[NH:25][CH:24]=3)[CH:16]12)=[O:14])[C:9]([CH3:12])([CH3:11])[CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH:8]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:13]([N:15]1[CH2:19][CH2:18][CH:17]2[N:20]([CH:33]3[CH2:34][CH2:35][CH2:36][CH2:37]3)[CH2:21][CH:22]([C:23]3[C:31]4[C:26](=[CH:27][C:28]([F:32])=[CH:29][CH:30]=4)[NH:25][CH:24]=3)[CH:16]12)=[O:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 67408721{1-[4-Cyclopentyl-6-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid tert-butyl ester

生成物 1

HCID 674083852-Amino-1-[4-cyclopentyl-6-(6-fluoro-1H-indol-3-yl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-3,3-dimethyl-butan-1-one収率 96.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution containing 38 (0.28 g, 0.53 mmol) in DCM (10 mL) was added TFA (3 mL) at ambient temperature. After 90 min, the reaction mixture was concentrated in vacuo. The residue was dissolved in EtOAc and the organic solution was washed successively with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford 218 mg of 39 which was used without further purification. 1H NMR (CDCl3, 300 MHz), mixture of rotamers: δ9.31 (s, 0.5H), 8.24 (s, 0.5H), 7.86 (dd, J=5.4, 8.7 Hz, 0.5H), 7.54 (dd, J=5.4, 8.7 Hz, 0.5H), 7.28 (s, 1H), 7.00 (dd, J=2.4, 9.9 Hz, 0.5H), 6.96-9.6.91 (m, 1H), 6.86-6.79 (m, 0.5H), 4.98 (app t, J=8.1 Hz, 0.5H), 4.80 (app t, J=7.8 Hz, 0.5H), 4.16-4.09 (m, 0.5H), 3.94-3.81 (m, 1.5H), 3.54-3.45 (m, 1H), 3.29-3.06 (m, 2H), 2.90-2.70 (m, 2H), 2.26-2.21 (m, 0.5H), 2.12-2.05 (m, 0.5H), 1.90-1.68 (m, 4H), 1.60-1.50 (m, 4H), 1.16 (br s, 2H), 0.80 (s, 4.5H), 0.21 (s, 4.5H) ppm. Mass spectrum, m/z [427.3] (M+H)+.

後処理

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washthe organic solution was washed successively with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-01f7a00d886f4e239d4f6a73b2e8f4cd
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08399683B2

反応ノート

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