ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Water → 4-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acid

HRID 1783878
ノート
印刷プレビュー

反応式

HRID 1783878 の反応式
[C:1]([O:5][C:6](=[O:33])[CH2:7][C@@H:8]([CH2:24][CH:25]1[CH2:32][CH2:31][C:28]2([CH2:30][CH2:29]2)[CH2:27][CH2:26]1)[C:9]([N:11]1[C@@H:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][O:13][C:12]1=[O:23])=[O:10])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.O>O1CCOCC1>[C:1]([O:5][C:6](=[O:33])[CH2:7][C@@H:8]([CH2:24][CH:25]1[CH2:26][CH2:27][C:28]2([CH2:29][CH2:30]2)[CH2:31][CH2:32]1)[C:9]([N:11]1[C@@H:15]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:14][O:13][C:12]1=[O:23])=[O:10])([CH3:4])([CH3:2])[CH3:3].[CH2:16]([C@H:15]1[CH2:14][O:13][C:12](=[O:23])[N:11]1[C:9](=[O:10])[C@H:8]([CH2:24][CH:25]1[CH2:32][CH2:31][C:28]2([CH2:29][CH2:30]2)[CH2:27][CH2:26]1)[CH2:7][C:6]([OH:33])=[O:5])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 684829284-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acid tert-butyl ester

生成物 2

HCID 684825934-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acid収率 278.1%
HCID 68482928
4-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

4-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acid tert-butyl ester was prepared according to the procedures described in Example 26. A modified procedure was used for the t-Butyl ester deprotection from Trzeciak, A. et al. Synthesis 1996, 1443. 4-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acid tert-butyl ester (40 mg, 0.09 mmol, 1.0 eq.) was dissolved in dry dioxane (5 mL) under nitrogen followed by addition of Et3N (200 μL, 1.43 mmol, 16 eq.) and TMS-OTf (200 μL, 1.11 mmol, 12.3 eq.) via syringe. The reaction mixture stirred at room temperature overnight and then heated to 65° C. for 1.5 hours. Upon completion, 2 mL of water was added and volatiles were evaporated. The product was diluted with ethyl ether and extracted with water, and brine. The organic layer was dried over MgSO4, filtered and evaporated to provide 4-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acid (50 mg, quantitative) as white solid and used directly in the next step. HPLC-MS calcd. for C23H29NO5 (M+Na+) 422.2, found 422.1. 4-(4-(S)-Benzyl-2-oxo-oxazolidin-3-yl)-4-oxo-3-(R)-spiro[2.5]oct-6-ylmethyl-butyric acid was converted to the title compound according to the procedures described in example 21.

後処理

  1. customet al. Synthesis 1996, 1443
  2. temperatureheated to 65° C. for 1.5 hours
  3. customvolatiles were evaporated
  4. additionThe product was diluted with ethyl ether
  5. extractionextracted with water, and brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-a19edd48a1ea4ba5bb67556f5e63ca3f
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07501408B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート