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

HRID 216275Notes

Reaction equation

HRID 216275 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-ab81840c474341fc862eb642da3c0310
Source dataset
uspto-grants-2012_06
Patent number
US08193227B2

Reaction notes

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