1,2-Dichloroethane → HCID 58813160、化合物

HRID 1391706ノート

反応式

HRID 1391706 の反応式
CCN(C(C)C)C(C)C.[CH2:10]([C@H:13]([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]([OH:16])=O)[CH:11]=[CH2:12].Cl.[NH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.Cl>CN(C=O)C>[CH2:10]([C@H:13]([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]([NH:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[O:16])[CH:11]=[CH2:12]

参加物

8

反応物 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 58813156HCID 58813156、化合物

生成物 1

HCID 58813160HCID 58813160、化合物収率 83%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Step B (1): DIEA (1.35 mL, 9.9 mmol) was added to a mixture of (S)-2-allylhexanoic acid (300 mg, 1.92 mmol), methyl 2-aminoacetate hydrochloride (254 mg, 2.02 mmol), EDC (387 mg, 2.02 mmol), HOBt (273 mg, 2.02 mmol) in DMF (15 mL) at room temperature. The mixture was stirred for 18 h. Poured the reaction mixture into 200 mL 1 M HCl. Extracted with EtOAc/Hex (95:5) (2×200 mL). Washed combined organic extracts with brine, dried with MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (5-50% EtOAc/hexanes linear gradient) to give (S)-methyl 2-(2-allylhexanamido)acetate 360 mg (83% yield) as white solid: ESI (M+H)+=228.2; 1H NMR (500 MHz, CDCl3) δ 5.90 (s, 1H), 5.64-5.85 (m, 1H), 4.95-5.14 (m, 2H), 4.04 (dd, J=5.04, 2.29 Hz, 2H), 3.75 (s, 3H), 2.28-2.46 (m, 1H), 2.07-2.29 (m, 2H), 1.62-1.64 (m, 1H), 1.46-1.47 (m, 1H), 1.18-1.36 (m, 4H), 0.87 (t, J=6.87 Hz, 3H).

後処理

  1. extractionExtracted with EtOAc/Hex (95:5) (2×200 mL)
  2. washWashed
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (5-50% EtOAc/hexanes linear gradient)

出典と根拠

ORDレコード
ord-9e89ec9dd99a4d778aac577667933761
出典データセット
uspto-grants-2008_03
特許番号
US07338974B2

反応ノート

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