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Sodium Bicarbonate → (S)-2-[1-(9-fluorenylmethyloxycarbonyl)-6-oxo-1,7-diazaspiro[4.4]non-7-yl]propionic acid

HRID 1263418
ノート
印刷プレビュー

反応式

HRID 1263418 の反応式
[C:1](=[O:4])([OH:3])[O-].[Na+].[O:6]=[C:7]1[N:15]([C@@H:16]([CH3:20])[C:17]([OH:19])=[O:18])[CH2:14][CH2:13][C:8]21[NH:12][CH2:11][CH2:10][CH2:9]2.C(=O)([O-])ON1C(=O)CC([CH2:29][CH:30]2[C:42]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[C:36]3[C:31]2=[CH:32][CH:33]=[CH:34][CH:35]=3)C1=O>O.CC(C)=O>[CH:32]1[C:31]2[CH:30]([CH2:29][O:3][C:1]([N:12]3[C:8]4([CH2:13][CH2:14][N:15]([C@@H:16]([CH3:20])[C:17]([OH:19])=[O:18])[C:7]4=[O:6])[CH2:9][CH2:10][CH2:11]3)=[O:4])[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:36]=2[CH:35]=[CH:34][CH:33]=1
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 3

HCID 516892Sodium BicarbonateHCID 54078033(S)-2-(6-oxo-1,7-diazaspiro[4.4]non-7-yl)propionic acidHCID 71304114(9H-fluoren-9-yl)methyl-2,5-dioxopyrrolidin-1-yl carbonate

生成物 1

HCID 53806324(S)-2-[1-(9-fluorenylmethyloxycarbonyl)-6-oxo-1,7-diazaspiro[4.4]non-7-yl]propionic acid

試薬・触媒・溶媒 2

HCID 180Acetone溶媒
HCID 962
Water
溶媒
2 回

実験手順

Excess solid sodium bicarbonate was added to (S)-2-(6-oxo-1,7-diazaspiro[4.4]non-7-yl)propionic acid (0.42 g) in water (2 ml) and then 9-fluorenylmethylsuccinimidyl carbonate (0.7 g) in acetone (3 ml) was added. The mixture was stirred for 18 hours. The mixture was then addled to water (10 ml), extracted with ether (10 ml) and the aqueous layer separated. (The ether extracts were discarded). The pH of the aqueous layer was adjusted to 3 with concentrated hydrochloric acid and then it was extracted with dichloromethane (2×10 ml). The combined extracts were separated, dried (MgSO4) and evaporated to give (S)-2-[1-(9-fluorenylmethyloxycarbonyl)-6-oxo-1,7-diazaspiro[4.4]non-7-yl]propionic acid (0.62 g) as a white foam; NMR (d6-DMSO (373K)): some doubling of peaks due to the mixture of diastereoisomers, 1.3 (2d, 3H), 1.6-2.0 (m, 6H), 3.05 (m, 1H), 3.2-3.45 (m, 3H), 4.2-4.4 (m, 1H), 4.5 (m, 1H), 6.2 (s, 2H), 7.35 (m, 4H), 7.8 (m, 4H).

後処理

  1. extractionextracted with ether (10 ml)
  2. customthe aqueous layer separated
  3. extractionit was extracted with dichloromethane (2×10 ml)
  4. customThe combined extracts were separated
  5. dry with materialdried (MgSO4)
  6. customevaporated

出典と根拠

ORDレコード
ord-48582f636153456cac2b13d28aecb648
出典データセット
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06541453B2

反応ノート

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