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

HRID 2284869노트

반응식

HRID 2284869 반응식
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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f8a36abcfc9f4680a1692ac6729b9839
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145437B2

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