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Tetrahydrofuran → tert-butyl{(1S,2R)-2-azido-2-[3,5-bis(trifluoromethyl)phenyl]-1-methylethyl}{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

HRID 1994510
ノート
印刷プレビュー

反応式

HRID 1994510 の反応式
C1(P([N:15]=[N+:16]=[N-:17])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:18]([O:22][C:23](=[O:65])[N:24]([C@@H:47]([CH3:64])[C@H:48]([C:50]1[CH:55]=[C:54]([C:56]([F:59])([F:58])[F:57])[CH:53]=[C:52]([C:60]([F:63])([F:62])[F:61])[CH:51]=1)O)[CH2:25][C:26]1[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[CH:28][C:27]=1C1C=C(C(C)C)C=CC=1OC)([CH3:21])([CH3:20])[CH3:19].C1C=CC(P([C:79]2[CH:84]=[CH:83][CH:82]=[CH:81]C=2)C2C=CC=CC=2)=CC=1.N(C(OCC)=O)=N[C:87](OCC)=O.[CH2:97]1[CH2:101][O:100][CH2:99][CH2:98]1>CCOC(C)=O>[C:18]([O:22][C:23](=[O:65])[N:24]([C@@H:47]([CH3:64])[C@H:48]([N:15]=[N+:16]=[N-:17])[C:50]1[CH:51]=[C:52]([C:60]([F:62])([F:61])[F:63])[CH:53]=[C:54]([C:56]([F:57])([F:58])[F:59])[CH:55]=1)[CH2:25][C:26]1[CH:31]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:29]=[CH:28][C:27]=1[C:97]1[CH:98]=[C:83]([CH:82]([CH3:81])[CH3:87])[CH:84]=[CH:79][C:101]=1[O:100][CH3:99])([CH3:19])([CH3:20])[CH3:21]
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 5

HCID 8028Tetrahydrofuran2 回HCID 11776Triphenylphosphine2 回HCID 199401P,P-Diphenylphosphinic azide2 回HCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 87121496Tert-butyl{(1s,2s)-2-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-1-methylethyl}{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

生成物 1

HCID 86603415tert-butyl{(1S,2R)-2-azido-2-[3,5-bis(trifluoromethyl)phenyl]-1-methylethyl}{[5'-isopropyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A dry flask was charged with THF (1 mL) diethyl azodicarboxylate (DEAD) (11 μL, 0.0698 mmol) and diphenylphosphoryl azide (DPPA) (15 μL, 0.0698 mmol). tert-butyl{(1S,2S)-2-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-1-methylethyl}{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate (20.7 mg, 0.0698 mmol) was added by cannula in THF (1 mL). Next Ph3P (18.3 mg, 0.0698 mmol) was added. The reaction was stirred at room temperature for 30 min, and then additional DEAD (11 μL, 0.0698 mmol), DPPA (15 μL, 0.0698 mmol), and Ph3P (18.3 mg, 0.0698 mmol) were added. After an additional 30 min, the reaction was diluted with EtOAc (40 mL) and washed with water and brine (15 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography with 15% EtOAc/hexanes afforded tert-butyl{(1S,2R)-2-azido-2-[3,5-bis(trifluoromethyl)phenyl]-1-methylethyl}{[5′-isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate. Rf=0.60 (25% EtOAc/hexanes). LCMS=619.3 (M+1−BOC)+.

後処理

  1. waitAfter an additional 30 min
  2. washwashed with water and brine (15 mL each)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the residue by flash chromatography with 15% EtOAc/hexanes

出典と根拠

ORDレコード
ord-55052fbf903543fca87f9601c5f2451b
出典データセット
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07652049B2

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