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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
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HRID 1263418 반응식
[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
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 180Acetone용매
HCID 962
Water
용매
2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-48582f636153456cac2b13d28aecb648
출처 데이터셋
uspto-grants-2003_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06541453B2

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