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Benzyl Alcohol → 3-[2-(3-Benzyloxycarbonylamino-2-oxo-2H-pyridin-1-yl)-2-tert-butoxycarbonyl-ethyl]-indole-1-carboxylic acid tert-butyl ester

HRID 1809487
ノート
印刷プレビュー

反応式

HRID 1809487 の反応式
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][C@@H:18]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[N:19]2[CH:24]=[CH:23][CH:22]=[C:21](C(O)=O)[C:20]2=[O:28])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:38]([CH2:41]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:50])C=CC=CC=1.[CH2:60]([OH:67])[C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH:18]([N:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH:38][C:41]([O:67][CH2:60][C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)=[O:50])[C:20]2=[O:28])[C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])=[CH:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]
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 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 58674953(S)-3-[2-tert-Butoxycarbonyl-2-(3-carboxy-2-oxo-2H-pyridin-1-yl)-ethyl]-indole-1-carboxylic acid tert-butyl ester

生成物 1

HCID 667016723-[2-(3-Benzyloxycarbonylamino-2-oxo-2H-pyridin-1-yl)-2-tert-butoxycarbonyl-ethyl]-indole-1-carboxylic acid tert-butyl ester
収率 59.8%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of (S)-3-[2-tert-Butoxycarbonyl-2-(3-carboxy-2-oxo-2H-pyridin-1-yl)-ethyl]-indole-1-carboxylic acid tert-butyl ester (1.8 g, 3.7 mmol) in dioxane was added triethylamine (580 mg, 5.9 mmol), diphenylphosphoryl azide 91.5 g, 5.6 mmol) and benzyl alcohol (680 mg, 6.3 mmol) and the mixture refluxed at 100 C for 18 hours. The mixture was concentrated and partitioned between ethylacetate and saturated bicarbonate. The organic layer was washed with brine, dried (MgSO4), filtered and evaporated to afford the crude product, which was purified by flash chromatography (30-70% ethylacetate/petroleum ether) to afford the title compound as a white solid (1.3 g, 59%); 1H NMR (400 MHz, CDCl3) δ 1.48 (9H, s), 1.73 (9H, s), 3.45 (1H, m), 3.65 (1H, m), 5.2-5.25 (2H, m), 5.60 (1H, m), 6.15 (1H, t), 6.85 (1H, m), 7.25-7.55 (9H, m), 7.95 (1H, m), 8.02-8.18 (2H, m);

後処理

  1. temperaturethe mixture refluxed at 100 C for 18 hours
  2. concentrationThe mixture was concentrated
  3. custompartitioned between ethylacetate and saturated bicarbonate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto afford the crude product, which
  9. customwas purified by flash chromatography (30-70% ethylacetate/petroleum ether)

出典と根拠

ORDレコード
ord-24bc448526e944389d0d63787a94d354
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08362043B2

反応ノート

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