Methyl N-(triethylammoniosulfonyl)carbamate → HCID 57550206, compound

HRID 1716846Notes

Reaction equation

HRID 1716846 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][C:12]1[CH:27]=[CH:26][C:15]([C:16]([NH:18][C@H:19]([C:22]([O:24][CH3:25])=[O:23])[CH2:20][OH:21])=O)=[CH:14][CH:13]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]2[O:21][CH2:20][CH:19]([C:22]([O:24][CH3:25])=[O:23])[N:18]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 68666149HCID 68666149, compound

Product 1

HCID 57550206HCID 57550206, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A stirred solution of methyl N-{4-[(1-methyl-1H-benzimidazol-2-yl)methyl]-benzoyl}-serinate (0.2 g, 0.55 mmol, 1.0 eq) in THF was treated with Burgess reagent (0.156 g, 0.65 mmol) and molecular sieves (1 g), stirred at 60° C. for 2 h, cooled to room temperature and concentrated under reduced pressure. The resultant residue was purified by column chromatography (silica, CHCl3:MeOH 5%) to afford the title compound in 52% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, DMSO-d6): 7.95 (s, 1H), 7.84 (d, J=8 Hz, 1H), 7.57 (d, J=8 Hz, 1H), 7.48 (d, J=8 Hz, 1H), 7.39 (d, J=8 Hz, 2H)), 7.16-7.21 (m, 1H), 5.60 (m, 1H), 4.95 (t, J=8.4 Hz, 1H), 4.57-4.60 (m, 1H), 4.38 (s, 2H), 4.26 (t, J=8.4 Hz, 1H), 3.78 (s, 3H). LCMS (ESI+) 350 (MH+).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe resultant residue was purified by column chromatography (silica, CHCl3:MeOH 5%)

Sources & evidence

ORD record
ord-f924b61f933d42babf1ecc419a3dcb4c
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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