Sodium Hydroxide → HCID 10295657、化合物

HRID 1295128ノート

反応式

HRID 1295128 の反応式
C([O:3][C:4](=[O:33])[CH2:5][CH:6]([N:10]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][C:20](=[O:32])[CH2:21][C:22]3[CH:31]=[CH:30][C:29]4[CH2:28][CH2:27][CH2:26][NH:25][C:24]=4[N:23]=3)=[CH:16][CH:17]=2)[CH:12]=[CH:11]1)[CH2:7][CH2:8][CH3:9])C.[OH-].[Na+]>C1COCC1.O>[N:23]1[C:24]2[NH:25][CH2:26][CH2:27][CH2:28][C:29]=2[CH:30]=[CH:31][C:22]=1[CH2:21][C:20]([NH:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[N:10]([CH:6]([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:33])=[O:3])[CH:11]=[CH:12]2)=[O:32]

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 67427797HCID 67427797、化合物

生成物 1

HCID 10295657HCID 10295657、化合物収率 81%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-[5-(2-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl-acetylamino)-indol-1-yl]-hexanoic acid ethyl ester (50 mg, 0.12 mmol) in THF (1.0 mL) was added a solution of NaOH (18 mg, 0.45 mmol) in H2O (0.15 mL), and stirred at ambient temperature for 14 h. Solvents were evaporated. To the resulting residue was added 1N HCl until the solution reached a pH of 5. The mixture was extracted with EtOAc/DCM (9:1) several times until the aqueous layer was free from product by TLC. The extracts were combined, dried over Na2SO4, concentrated, and flash chromatographed on silica gel, eluting with MeOH/DCM (2.5, 5, and 7.5%) to afford the title compound (38 mg, 81% yield) as a pale brown solid. 1H NMR (CDCl3) δ 7.79 (d, 1H, J=1.9 Hz), 7.57 (d, 1H, J=7.3 Hz), 7.45 (d, 1H, J=8.9 Hz,), 7.34 (d, 1H, J=3.2 Hz), 7.23 (dd, 1H, J=2.0, 8.8 Hz), 6.69 (d, 1H, J=7.3 Hz), 6.46 (d, 1H, J=3.2 Hz), 3.83 (s, 0.9 H), 3.81 (s, 0.5H), 3.49 (t, 2H, J=5.6 Hz), 2.89 (d, 2H, J=7.2 Hz), 2.83 (t, 2H, J=6.1 Hz), 2.67–1.86 (m, 4H), 1.19–0.99 (m, 2H), 0.86 (t, 3H, J=7.3 Hz). Mass spectrum (LCMS, ESI) calculated for C24H29N4O3 421.2 (M+H); found 421.3.

後処理

  1. customSolvents were evaporated
  2. additionTo the resulting residue was added 1N HCl until the solution
  3. extractionThe mixture was extracted with EtOAc/DCM (9:1) several times until the aqueous layer
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customflash chromatographed on silica gel
  7. washeluting with MeOH/DCM (2.5, 5, and 7.5%)

出典と根拠

ORDレコード
ord-ca407e737a474dd0adb40245f3c68af4
出典データセット
uspto-grants-2007_07
特許番号
US07241789B2

反応ノート

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