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Dimethylcarbamoyl Chloride → tert-Butyl 2-(3-Methoxycarbonyladamant-1-ylcarbonylamino)-5-(N,N-dimethylaminocarbonyl)pent-4-ynoate

HRID 1242838
ノート
印刷プレビュー

反応式

HRID 1242838 の反応式
[CH3:1][O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][C:7]([C:15]([NH:17][CH:18]([CH2:26][C:27]#[CH:28])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:16])([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4].CCN(CC)CC.[CH3:36][N:37]([CH3:41])[C:38](Cl)=[O:39]>CN(C=O)C.[Cu]I>[CH3:1][O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][C:7]([C:15]([NH:17][CH:18]([CH2:26][C:27]#[C:28][C:38]([N:37]([CH3:41])[CH3:36])=[O:39])[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])=[O:16])([CH2:8]3)[CH2:6]1)[CH2:12]2)=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 21940505tert-Butyl 2-(3-methoxycarbonyladamant-1-ylcarbonylamino)pent-4-ynoate

生成物 1

HCID 21940493tert-Butyl 2-(3-Methoxycarbonyladamant-1-ylcarbonylamino)-5-(N,N-dimethylaminocarbonyl)pent-4-ynoate

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
触媒
HCID 6228Dimethylformamide溶媒

実験手順

The compound from Step A of Example 49 (0.389 g, 1 mmol) was dissolved in dry DMF (5 mL) with dichlorobis(diphenylphosphine)palladium (II) (0.02 eq), CuI (0.02 eq), Et3N (0.4 eq, 3 mL), and N,N-dimethylcarbamyl chloride (1.0 eq, 92 μL). The reaction mixture was stirred overnight at room temperature and then at 70° C. for 1 hour. The mixture was filtered through a pad of Celite and the solvent removed under reduced pressure. The crude product was purified by column chromatography (silica gel; EtOAc/hexanes, 2:3) to afford the title compound.

後処理

  1. waitat 70° C. for 1 hour
  2. filtrationThe mixture was filtered through a pad of Celite
  3. customthe solvent removed under reduced pressure
  4. customThe crude product was purified by column chromatography (silica gel; EtOAc/hexanes, 2:3)

出典と根拠

ORDレコード
ord-54efcf2befb84b4984eeaa5aea6c51b7
出典データセット
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07115768B2

反応ノート

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