tert-Butanol → 1-Benzyloxycarbonyl-4-(R)-(1-tert-butoxycarbonylaminocyclopropyl)-3-(R)-methoxypyrrolidine

HRID 635076ノート

反応式

HRID 635076 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][CH3:17])[C@@H:13]([C:18]2(C(O)=O)[CH2:20][CH2:19]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.C([N:43]([CH2:46]C)CC)C.[C:48]([OH:52])([CH3:51])([CH3:50])[CH3:49]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][C@H:13]([C:18]2([NH:43][C:46]([O:52][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:31])[CH2:19][CH2:20]2)[C@@H:14]([O:16][CH3:17])[CH2:15]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 542347281-[1-Benzyloxycarbonyl-4-(R)-methoxy-3-(S)-pyrrolidinyl]cyclopropanecarboxylic acid

生成物 1

HCID 219712631-Benzyloxycarbonyl-4-(R)-(1-tert-butoxycarbonylaminocyclopropyl)-3-(R)-methoxypyrrolidine収率 50%

実験手順

1-[1-Benzyloxycarbonyl-4-(R)-methoxy-3-(S)-pyrrolidinyl]cyclopropanecarboxylic acid (713 mg, 2.22 mmol) was dissolved in tert-butyl alcohol (20 ml), and the solution was mixed with diphenylphosphoryl azide (623 μl, 2.89 mmol) and triethylamine (775 μl, 5.56 mmol), stirred at room temperature for 20 minutes and then heated under reflux for 19 hours. The reaction solution was cooled and then concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography and eluted with an eluant of n-hexane:ethyl acetate=3:2, to thereby obtain the title compound (431 mg, 50%) as a colorless oil.

後処理

  1. temperatureheated
  2. temperatureunder reflux for 19 hours
  3. temperatureThe reaction solution was cooled
  4. concentrationconcentrated under reduced pressure
  5. washeluted with an eluant of n-hexane

出典と根拠

ORDレコード
ord-64fa3429436f4391a76428d487d8ae0a
出典データセット
uspto-grants-2001_02
特許番号
US06184388B2

反応ノート

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