Triethylamine → Tert-butyl(1s,2r)-1-benzyl-2-hydroxy-3-{isobutyl[(4-vinylphenyl)sulfonyl]amino}propylcarbamate

HRID 243586ノート

反応式

HRID 243586 の反応式
[CH2:1]([C@H:8]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C@H:9]([OH:16])[CH2:10][NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:30][CH3:31])CC)C.C([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[S:40](Cl)(=[O:42])=[O:41])=C>ClCCl>[CH2:1]([C@H:8]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[C@H:9]([OH:16])[CH2:10][N:11]([CH2:12][CH:13]([CH3:15])[CH3:14])[S:40]([C:35]1[CH:36]=[CH:37][C:38]([CH:30]=[CH2:31])=[CH:39][CH:34]=1)(=[O:42])=[O:41])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 9902339tert-Butyl ((2S,3R)-3-hydroxy-4-((2-methylpropyl)amino)-1-phenylbutan-2-yl)carbamateHCID 21983175Vinylbenzenesulfonyl chloride

生成物 1

HCID 91062328Tert-butyl(1s,2r)-1-benzyl-2-hydroxy-3-{isobutyl[(4-vinylphenyl)sulfonyl]amino}propylcarbamate収率 54%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of Example 1 (11.86 g) in dichloromethane (100 mL) was added triethylamine (TEA) (19.6 mL, 4 equivalents) followed by dropwise addition of vinylbenzenesulfonyl chloride (8.36 g, 1.2 equivalents) at 25° C. for 3 hrs. The mixture was partitioned in 1N sodium bicarbonate (NaHCO3) and ethyl acetate (EtOAc). The organic extract was concentrated, and the residue was chromatographed on silica gel, eluting with ethyl acetate/hexanes (1:4) to afford the title compound (9.6 g, 54%). 1H NMR (300 MHz, CDCl3): δ ppm 0.87 (d, J=6.44 Hz, 3H), 0.90 (d, J=6.78 Hz, 3H), 1.34 (s, 9H), 1.86 (m, 1H), 2.84 (dd, J=13.39, 6.61 Hz, 2H), 2.97 (m, 3H), 3.11 (m, 3H), 3.79 (s, 1H), 4.61 (s, 1H), 5.44 (d, J=10.85 Hz, 1H), 5.88 (d, J=17.63 Hz, 1H), 6.75 (dd, J=17.63, 10.85 Hz, 1H), 7.25 (m, 5H), 7.51 (d, J=8.48 Hz, 2H), 7.72 (d, J=8.48 Hz, 2H).

後処理

  1. customThe mixture was partitioned in 1N sodium bicarbonate (NaHCO3)
  2. extractionThe organic extract
  3. concentrationwas concentrated
  4. customthe residue was chromatographed on silica gel
  5. washeluting with ethyl acetate/hexanes (1:4)

出典と根拠

ORDレコード
ord-5cdb2b8d525c4e1095f3901836b70280
出典データセット
uspto-grants-2014_02
特許番号
US08653141B2

反応ノート

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