Triethylamine → Tert-butyl 9-[2-(isobutylcarbamoylamino)acetyl]-4,9-diazaspiro[5.5]-undecane-4-carboxylate

HRID 2284869ノート

反応式

HRID 2284869 の反応式
Cl.C1[C:7]2(C[CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)CNCC1.[CH2:20]([NH:24][C:25]([NH:27][CH2:28][C:29]([OH:31])=O)=[O:26])[CH:21]([CH3:23])[CH3:22].C(N(CC)CC)C.CN(C(ON1N=N[C:49]2[CH:50]=[CH:51][CH:52]=[N:53][C:48]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.C(OCC)(=O)C.CN(C)C=O>[CH2:20]([NH:24][C:25]([NH:27][CH2:28][C:29]([N:53]1[CH2:48][CH2:49][C:50]2([CH2:7][CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:11]2)[CH2:51][CH2:52]1)=[O:31])=[O:26])[CH:21]([CH3:22])[CH3:23]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16785937(Isobutylcarbamoyl)glycineHCID 71464197Tert-butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride

生成物 1

HCID 118022279Tert-butyl 9-[2-(isobutylcarbamoylamino)acetyl]-4,9-diazaspiro[5.5]-undecane-4-carboxylate

試薬・触媒・溶媒 3

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

実験手順

To a round bottom flask add tert-butyl 4,9-diazaspiro[5.5]undecane-9-carboxylate hydrochloride (1.38 mmol), 2-(isobutylcarbamoylamino)acetic acid (1.15 mmol), dimethylformamide (3.8 mL), triethylamine (1.72 mmol), and HATU (1.26 mmol. Stir at room temperature for 16 hours, then dilute with water (50 mL) and ethyl acetate (50 mL). Wash the organic phase with concentrated ammonium chloride (50 mL) and brine (50 mL). Dry the organics over sodium sulfate, filter, and concentrate under reduced pressure. Purify the intermediate by flash chromatography (40 g silica gel cartridge) eluting with 0-10% methanol in ethyl acetate to yield tert-butyl 9-[2-(isobutylcarbamoylamino)acetyl]-4,9-diazaspiro[5.5]-undecane-4-carboxylate (0.38 g, 0.93 mmol): MS (m/z): 411.2 (M+H).

後処理

  1. washWash the organic phase with concentrated ammonium chloride (50 mL) and brine (50 mL)
  2. dry with materialDry the organics over sodium sulfate
  3. filtrationfilter
  4. concentrationconcentrate under reduced pressure
  5. customPurify the intermediate by flash chromatography (40 g silica gel cartridge)
  6. washeluting with 0-10% methanol in ethyl acetate

出典と根拠

ORDレコード
ord-f8a36abcfc9f4680a1692ac6729b9839
出典データセット
uspto-grants-2015_09
特許番号
US09145437B2

反応ノート

読み込み中…