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4-Methylmorpholine → (1R,10R,11S,16S)-3-hydroxy-1,11,15,15-tetramethyl-5-[(4-methyl piperazin-1-yl)-carbonyl]-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-8,8-dione

HRID 422179
ノート
印刷プレビュー

反応式

HRID 422179 の反応式
C[O:2][C:3]1[CH:20]=[C:19]([C:21]([OH:23])=O)[CH:18]=[C:17]2[C:4]=1[C@H:5]1[C@H:14]([CH2:15][S:16]2(=[O:25])=[O:24])[C@:13]2([CH3:26])[C@H:8]([C:9]([CH3:28])([CH3:27])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]1.[CH3:29]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[CH3:60][N:61]1[CH2:66][CH2:65][NH:64][CH2:63][CH2:62]1>C1COCC1.CN(C=O)C>[OH:2][C:3]1[CH:20]=[C:19]([C:21]([N:64]2[CH2:65][CH2:66][N:61]([CH3:60])[CH2:62][CH2:63]2)=[O:23])[CH:18]=[C:17]2[C:4]=1[C@@:5]1([CH3:29])[C@H:14]([CH2:15][S:16]2(=[O:24])=[O:25])[C@:13]2([CH3:26])[C@H:8]([C:9]([CH3:28])([CH3:27])[CH2:10][CH2:11][CH2:12]2)[CH2:7][CH2:6]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 79724-MethylmorpholineHCID 531671-MethylpiperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86654189(1R,10S,11S,16S)-3-methoxy-11,15,15-trimethyl-8,8-dioxo-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylic acid

生成物 1

HCID 53240855
(1R,10R,11S,16S)-3-hydroxy-1,11,15,15-tetramethyl-5-[(4-methyl piperazin-1-yl)-carbonyl]-8lambda6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-8,8-dione
収率 54.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of (1R,10S,11S,16S)-3-methoxy-11,15,15-trimethyl-8,8-dioxo-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-5-carboxylic acid (61) (0.20 g, 0.49 mmol), HATU (0.37 g, 0.98 mmol), N-methylmorpholine (0.10 mL, 1.5 mmol) and 1-methylpiperazine (0.15 mL, 1.5 mmol) in THF (10 mL) and DMF (2.0 mL) was stirred at room temperature for 18 h. The THF was evaporated under reduced pressure, the residue was quenched with water and the resulting solid was collected by filtration. The crude product was purified by flash column chromatography on silica gel (CH2Cl2/MeOH, 10:1) to give (1R,10R,11S,16S)-3-hydroxy-1,11,15,15-tetramethyl-5-[(4-methyl piperazin-1-yl)-carbonyl]-8λ6-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene-8,8-dione (89) (0.13 g, 54%) as a white solid. 1H NMR (CDCl3): δ 9.55 (s, 1H), 7.23 (d, 1H), 7.07 (d, 1H), 3.84 (m, 2H), 3.49 (m, 2H), 3.18 (m, 3H), 2.52 (m, 2H), 2.38 (m, 2H), 2.33 (s, 3H), 2.15 (d, 1H), 1.78-1.32 (m, 6H), 1.28 (s, 3H), 1.24-1.05 (m, 2H), 0.98 (m, 1H), 0.90 (s, 6H), 0.86 (m, 1H), 0.82 (s, 3H). MS m/z 489 (C27H40N2O4S+H+).

後処理

  1. customThe THF was evaporated under reduced pressure
  2. customthe residue was quenched with water
  3. filtrationthe resulting solid was collected by filtration
  4. customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2/MeOH, 10:1)

出典と根拠

ORDレコード
ord-0c1f1719b2a24bc5bc5ea312aa191343
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08101605B2

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