Triphenylphosphine → N-{2-[(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-{(3-methylbutyl)[(4-nitrophenyl)sulfonyl]amino}butyl]phenyl}-Nalpha-(methoxycarbonyl)-beta-phenyl-L-phenylalaninamide

HRID 714132ノート

反応式

HRID 714132 の反応式
[Si:1]([O:18][CH2:19][C@@H:20]([NH:51][S:52]([C:55]1[CH:60]=[CH:59][C:58]([N+:61]([O-:63])=[O:62])=[CH:57][CH:56]=1)(=[O:54])=[O:53])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][C:30](=[O:50])[C@H:31]([CH:37]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[NH:32][C:33]([O:35][CH3:36])=[O:34])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:83](O)[CH2:84][CH:85]([CH3:87])[CH3:86].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Si:1]([O:18][CH2:19][C@@H:20]([N:51]([CH2:83][CH2:84][CH:85]([CH3:87])[CH3:86])[S:52]([C:55]1[CH:56]=[CH:57][C:58]([N+:61]([O-:63])=[O:62])=[CH:59][CH:60]=1)(=[O:53])=[O:54])[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][C:30](=[O:50])[C@H:31]([CH:37]([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[NH:32][C:33]([O:35][CH3:36])=[O:34])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 31260Isoamyl AlcoholHCID 5363146Diisopropyl azodicarboxylateHCID 86708031N-{2-[(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-{[(4-nitrophenyl)sulfonyl]amino}butyl]phenyl}-Nalpha-(methoxycarbonyl)-beta-phenyl-L-phenylalaninamide

生成物 1

HCID 86708032N-{2-[(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-{(3-methylbutyl)[(4-nitrophenyl)sulfonyl]amino}butyl]phenyl}-Nalpha-(methoxycarbonyl)-beta-phenyl-L-phenylalaninamide収率 83%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of N-{2-[(3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-{[(4-nitrophenyl)sulfonyl]amino}butyl]phenyl}-Nα-(methoxycarbonyl)-β-phenyl-L-phenylalaninamide (9, 160 mg, 0.181 mmol), Ph3P (149 mg, 0.568 mmol) and isoamyl alcohol (89 mg, 1.01 mmol) (or any other suitable alcohol) in THF (1.5 ml) stirred at external temperature of 0° C. under N2 atmosphere, was treated with neat DIAD (150 μL, 0.771 mmol) and the mixture stirred at the same temperature for 30 min and then at room temperature in the dark for 16 h, concentrated and purified in a cromatographic cartridge of silicagel (24 g) eluted with 10% to 40% EtOAc in hexane, to get 143 mg (83%) of the title compound as white foam MS: m/z=955.3 (MH+).

後処理

  1. waitat room temperature in the dark for 16 h
  2. concentrationconcentrated
  3. custompurified in a cromatographic cartridge of silicagel (24 g)
  4. washeluted with 10% to 40% EtOAc in hexane

出典と根拠

ORDレコード
ord-864f13b25010429c800579de744beb2e
出典データセット
uspto-grants-2015_11
特許番号
US09187415B2

反応ノート

読み込み中…