Triethylamine → HCID 178441265、化合物

HRID 1888687ノート

反応式

HRID 1888687 の反応式
CCN=C=NC[CH2:7][CH2:8][N:9]([CH3:11])C.Cl.[CH2:13]([C:17]1=[CH:18][N:19]([C:36]([CH3:39])([CH3:38])[CH3:37])[S:20]/[C:21]/1=[N:22]\[C:23]([C@:25]1([CH3:35])[CH2:29][CH2:28][C@H:27]([C:30]([OH:32])=O)[C:26]1([CH3:34])[CH3:33])=[O:24])[CH2:14][CH2:15][CH3:16].OC1C2N=NNC=2C=CC=1.Cl.N1CCC1.C(N(CC)CC)C>C(OCC)(=O)C.O.CN(C)C=O>[N:9]1([C:30]([C@H:27]2[CH2:28][CH2:29][C@@:25]([CH3:35])([C:23](/[N:22]=[C:21]3/[C:17]([CH2:13][CH2:14][CH2:15][CH3:16])=[CH:18][N:19]([C:36]([CH3:38])([CH3:37])[CH3:39])[S:20]/3)=[O:24])[C:26]2([CH3:33])[CH3:34])=[O:32])[CH2:8][CH2:7][CH2:11]1

参加物

9

反応物 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12308726Azetidine hydrochlorideHCID 178418300HCID 178418300、化合物HCID 178441278HCID 178441278、化合物

生成物 1

HCID 178441265HCID 178441265、化合物収率 58.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Solid N-(3-dimethylaminopropyl)-n′-ethylcarbodiimide hydrochloride (EDC) (Aldrich, 216 mg, 1.12 mmol), the product from Example 173 (296 mg, 0.750 mmol), hydroxybenzotriazole (Aldrich, 152 mg, 1.12 mmol), azetidine hydrochloride (Aldrich, 105 mg, 1.12 mmol), triethylamine (Aldrich, 152 mg, 1.50 mmol) and anhydrous N,N-dimethylformamide (4 mL) were mixed together at room temperature. Water was added to quench and the mixture was extracted with dichloromethane. The extracts were dried over sodium sulfate and concentrated by rotary evaporator to give a brown oil. Flash chromatography (silica gel: 20-75% ethyl acetate in hexanes) afforded 189 mg (58%) of the title compound. 1H NMR (DMSO-d6) δ 0.50 (s, 3H), 0.90 (t, J=7.8 Hz, 3H), 1.22 (s, 3H), 1.23 (s, 3H), 1.23-1.35 (m, 4H), 1.37-1.46 (m, 1H), 1.56 (s, 9H), 1.56-1.67 (m, 2H), 1.90-2.03 (m, 1H), 2.08-2.22 (m, 2H), 2.71-2.76 (m, 2H), 2.77-2.83 (m, 1H), 3.73-3.81 (m, 1H), 3.82-3.91 (m, 1H), 4.06-4.14 (m, 1H), 4.18-4.26 (m, 1H), 8.50 (s, 1H). MS (ESI+) m/z 434 (M+H)+. Anal. calcd. for C24H39N3O2S: C, 66.47; H, 9.06; N, 9.69. Found: C, 66.60; H, 9.02; N, 9.47.

後処理

  1. customto quench
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe extracts were dried over sodium sulfate
  4. concentrationconcentrated by rotary evaporator
  5. customto give a brown oil

出典と根拠

ORDレコード
ord-c999a571b3d54a32a6b4c64fe46af011
出典データセット
uspto-grants-2013_08
特許番号
US08501794B2

反応ノート

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