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Hydrochloric Acid → (S)-[1-[[[[4-[[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-1-(phenylmethyl)-2-pyridinyl]methyl]-2,3-dioxo-1-piperazinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

HRID 1252616
ノート
印刷プレビュー

反応式

HRID 1252616 の反応式
[C:1]1([CH2:7][O:8][C:9]([NH:11][C@H:12]2[CH2:15][NH:14][C:13]2=[O:16])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[S:18]([N:21]=[C:22]=[O:23])(=[O:20])=[O:19].C(N(CC)CC)C.[O:31]=[C:32]1[C:37]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[CH:36][N:35]([CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:34]([CH2:53][N:54]2[CH2:59][CH2:58][NH:57][C:56](=[O:60])[C:55]2=[O:61])=[CH:33]1.CN([Si](C)(C)C)C(=O)C(F)(F)F.Cl>C(OCC)(=O)C.ClCCl>[O:31]=[C:32]1[C:37]([O:38][CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[CH:36][N:35]([CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:34]([CH2:53][N:54]2[CH2:59][CH2:58][N:57]([S:18]([NH:21][C:22]([N:14]3[CH2:15][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:13]3=[O:16])=[O:23])(=[O:20])=[O:19])[C:56](=[O:60])[C:55]2=[O:61])=[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

9

反応物 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 70918Chlorosulfonyl isocyanateHCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamateHCID 141824891-[[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-1-(phenylmethyl)-2-pyridinyl]methyl]-2,3-piperazinedione

生成物 1

HCID 86742166(S)-[1-[[[[4-[[1,4-Dihydro-4-oxo-5-(phenylmethoxy)-1-(phenylmethyl)-2-pyridinyl]methyl]-2,3-dioxo-1-piperazinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester収率 77.4%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of (S)-3-[[(phenylmethoxy)carbonyl]amino]-2-azetidinone (0.44 g, 2.0 mmol) in 25 ml of dry ethyl acetate was added 0.28 g (2.0 mmol) of chlorosulfonyl isocyanate and the solution was stirred for 30 minutes at room temperature. To this were added 12 ml of dichloromethane, 0.61 g (6 mmol) of triethylamine and a prestirred (three hours) mixture of 1-[[1,4-dihydro-4-oxo-5-(phenylmethoxy)-1-(phenylmethyl)-2-pyridinyl]methyl]-2,3-piperazinedione (0.83 g, 2.0 mmol) and N-methyl-N-(trimethylsilyl)trifluoroacetamide (1.59 g, 8.0 mmol) in 25 ml of dry ethyl acetate. After stirring for three days at room temperature, ice water was added and the pH was adjusted to one with hydrochloric acid. The insoluble residue was filtered off and dried in vacuo yielding 1.15 g of the title compound of 72% purity.

後処理

  1. stirringa prestirred
  2. stirringAfter stirring for three days at room temperature
  3. filtrationThe insoluble residue was filtered off
  4. customdried in vacuo

出典と根拠

ORDレコード
ord-630d176e5d504756a60b7d3530e277c3
出典データセット
uspto-grants-1988_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04743685

反応ノート

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