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

Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-butyl 4-(1-cyano-2-(4'-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

HRID 216905
ノート
印刷プレビュー

反応式

HRID 216905 の反応式
NC(=O)[C@@H](NC(C1(NC(=O)OC(C)(C)C)CCOCC1)=O)CC1C=CC(C2C=CC(C(F)(F)F)=CC=2)=CC=1.[NH2:39][C:40](=O)[C@@H:41]([NH:60][C:61]([C:63]1([NH:69][C:70](=[O:76])[O:71][C:72]([CH3:75])([CH3:74])[CH3:73])[CH2:68][CH2:67][O:66][CH2:65][CH2:64]1)=[O:62])[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52]([S:55]([CH2:58][CH3:59])(=[O:57])=[O:56])=[CH:51][CH:50]=2)=[CH:45][CH:44]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>ClCCl>[C:40]([C@@H:41]([NH:60][C:61]([C:63]1([NH:69][C:70](=[O:76])[O:71][C:72]([CH3:75])([CH3:74])[CH3:73])[CH2:68][CH2:67][O:66][CH2:65][CH2:64]1)=[O:62])[CH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52]([S:55]([CH2:58][CH3:59])(=[O:57])=[O:56])=[CH:51][CH:50]=2)=[CH:45][CH:44]=1)#[N:39]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59568598(S)-tert-butyl 4-(1-amino-1-oxo-3-(4'-(trifluoromethyl)biphenyl-4-yl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamateHCID 59568601(S)-tert-butyl 4-(1-amino-3-(4'-(ethylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

生成物 1

HCID 59568561(S)-tert-butyl 4-(1-cyano-2-(4'-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The mixture of (S)-tert-butyl 4-(1-amino-1-oxo-3-(4′-(trifluoromethyl)biphenyl-4-yl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate and (S)-tert-butyl 4-(1-amino-3-(4′-(ethylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 1, step (iv), 1.7 g) in dichloromethane (15 mL) was treated with Burgess' reagent (1.19 g) and the mixture was stirred at room temperature for 72 h. The reaction was evaporated onto silica and purified on a silica column eluting with 20% ethyl acetate in isohexane, then 50% ethyl acetate in isohexane and finally 100% ethyl acetate to afford after evaporation of the relevant fractions (S)-tert-butyl 4-(1-cyano-2-(4′-(trifluoromethyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (650 mg) and (S)-tert-butyl 4-(1-cyano-2-(4′-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (920 mg).

後処理

  1. customThe reaction was evaporated onto silica
  2. custompurified on a silica column
  3. washeluting with 20% ethyl acetate in isohexane
  4. custom50% ethyl acetate in isohexane and finally 100% ethyl acetate to afford
  5. customafter evaporation of the relevant fractions (S)-tert-butyl 4-(1-cyano-2-(4′-(trifluoromethyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (650 mg) and (S)-tert-butyl 4-(1-cyano-2-(4′-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (920 mg)

出典と根拠

ORDレコード
ord-52e35b59fc9f4f55a3495e97bf1c4c39
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08193239B2

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