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Hydrochloric Acid → tert-Butyl (2S)-1-oxo-1-(2-(tetrahydro-2H-pyran-3-ylcarbamoyl)-1H-pyrrol-1-ylamino)propan-2-ylcarbamate

HRID 525039
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HRID 525039 반응식
C(N(CC)CC)C.[O:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH2:14])[CH2:9]1.Cl.[C:16]([O:20][C:21]([NH:23][C@@H:24]([CH3:37])[C:25]([NH:27][N:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33](OC)=[O:34])=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C[Al](C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[O:26]=[C:25]([NH:27][N:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[C:33](=[O:34])[NH:14][CH:10]1[CH2:11][CH2:12][CH2:13][O:8][CH2:9]1)[C@@H:24]([NH:23][C:21](=[O:22])[O:20][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:37]
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참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 13355Disodium 2,3-dihydroxybutanedioateHCID 5200320Oxan-3-amineHCID 16682925TrimethylaluminumHCID 86722033(S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate

생성물 1

HCID 86722058
tert-Butyl (2S)-1-oxo-1-(2-(tetrahydro-2H-pyran-3-ylcarbamoyl)-1H-pyrrol-1-ylamino)propan-2-ylcarbamate

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매3회

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온도
80 °C

실험 절차

Anhydrous triethylamine (600 μl, 4.31 mmols) was added to a solution of tetrahydro-2H-pyran-3-amine.HCl (600 mg, 4.36 mmols) in toluene (10 ml) and it was stirred at room temperature for 30 min. A solution of (S)-methyl 1-(2-(tert-butoxycarbonylamino)propanamido)-1H-pyrrole-2-carboxylate (900 mg, 2.90 mmols) in toluene (36 ml) and a 2M solution of trimethylaluminium in toluene (7 ml, 14 mmols) were added. The solution obtained was stirred at 80° C. for 2 h. Water (70 ml) and a 0.5M sodium tartrate solution (35 ml) were added. It was extracted with ethylacetate. The combined organic layers were washed with water and brine. It was dried, filtered and concentrated in vacuum. The title compound was obtained (750 mg, 68%).

후처리

  1. customThe solution obtained
  2. extractionIt was extracted with ethylacetate
  3. washThe combined organic layers were washed with water and brine
  4. customIt was dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum

출처 및 근거

ORD 기록
ord-4f3c9e4f3b6c45da880bdcf15a7164fb
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09340547B2

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