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

HRID 243586노트

반응식

HRID 243586 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5cdb2b8d525c4e1095f3901836b70280
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653141B2

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