Sodium Carbonate → HCID 58864226, compound

HRID 2250189Notes

Reaction equation

HRID 2250189 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:5][C:6]1[CH:15]=[CH:14][C:9]2[NH:10][C:11]([CH3:13])=[N:12][C:8]=2[CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:34][Si:35]([CH3:43])([CH3:42])[CH2:36][CH2:37][S:38](Cl)(=[O:40])=[O:39]>C(#N)C>[CH3:1][O:2][C:3](=[O:27])[C@H:4]([NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:5][C:6]1[CH:15]=[CH:14][C:9]2[N:10]([S:38]([CH2:37][CH2:36][Si:35]([CH3:43])([CH3:42])[CH3:34])(=[O:40])=[O:39])[C:11]([CH3:13])=[N:12][C:8]=2[CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 98370862-(Trimethylsilyl)ethane-1-sulfonyl chlorideHCID 178501362HCID 178501362, compound

Product 1

HCID 58864226HCID 58864226, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of (R)-2-benzyloxycarbonylamino-3-(2-methyl-1H-benzoimidazol-5-yl)-propionic acid methyl ester (533 mg, 1.96 mmol), and sodium carbonate in acetonitrile (20 mL) was added neat 2-trimethylsilanylethanesulfonyl chloride all at once. The mixture was stirred at room temperature overnight. Solvents were removed and the residue was purified by chromatography on silica gel using ethyl acetate/hexanes (1:2) as eluent to afford the title compound as a waxy solid (1:1 mixture of N1 and N3 isomers, 66%). 1H-NMR (CDCl3, 500 MHz) δ 7.68 (d, J=8.5 Hz, 0.5H), 7.55 (d, J=8.5 Hz, 0.5H), 7.53 (s, 0.5H), 7.41 (s, 0.5H), 7.34-7.29 (m, 5H), 7.06-7.04 (m, 1H), 5.22 (d, J=8.0 Hz, 0.5H), 5.17 (d, J=7.5 Hz, 0.5H), 5.11-5.07 (m, 2H), 4.72-4.69 (m, 1H), 3.75 (s, 1.5H), 3.72 (s, 1.5H), 3.24-3.17 (m, 2H), 2.79 (s, 3H), 0.92-0.83 (m, 2H), −0.02 (s, 4.5H), −0.05 (s, 4.5H). Mass spec.: 532.26 (MH)+.

Workup

  1. customSolvents were removed
  2. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8b66fa9467f449b5a1062a552466d75f
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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