Diisopropylethylamine → (1-{4-[Methyl-(tetrahydro-pyran-4-carbonyl)-amino]-benzenesulfonyl}-piperidin-4-yl)-carbamic acid tert-butyl ester

HRID 337212ノート

反応式

HRID 337212 の反応式
[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][CH3:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[O:35]1[CH2:40][CH2:39][CH:38]([C:41](Cl)=[O:42])[CH2:37][CH2:36]1>C1COCC1>[C:1]([O:5][C:6](=[O:25])[NH:7][CH:8]1[CH2:9][CH2:10][N:11]([S:14]([C:17]2[CH:18]=[CH:19][C:20]([N:23]([CH3:24])[C:41]([CH:38]3[CH2:39][CH2:40][O:35][CH2:36][CH2:37]3)=[O:42])=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH2:12][CH2:13]1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 2795505Oxane-4-carbonyl chlorideHCID 71060136[1-(4-Methylamino-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

生成物 1

HCID 71060228(1-{4-[Methyl-(tetrahydro-pyran-4-carbonyl)-amino]-benzenesulfonyl}-piperidin-4-yl)-carbamic acid tert-butyl ester収率 100.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

[1-(4-Methylamino-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.13 g, 0.35 mmol) was dissolved in THF (5 ml). To this was added diisopropylethylamine (0.18 ml, 0.7 mmol) in one portion followed by the drop wise addition of tetrahydro-2H-pyran-4-carbonyl chloride (0.06 ml, 0.38 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the mixture was concentrated, diluted with DCM (200 ml) and washed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated to give the title compound (0.17 g, 98% yield) as a white powder which was taken on without further purification. Tr=1.89 min m/z (ES+) (M+Na+) 504.

後処理

  1. concentrationAfter this time the mixture was concentrated
  2. additiondiluted with DCM (200 ml)
  3. washwashed sequentially with HCl (1M solution, 10 ml), NaOH (1M solution, 10 ml) and brine (10 ml)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-53cebd2059fb423499af9799a08148ee
出典データセット
uspto-grants-2014_11
特許番号
US08889716B2

反応ノート

読み込み中…