Methyl N-(triethylammoniosulfonyl)carbamate → HCID 68461440, compound

HRID 507433Notes

Reaction equation

HRID 507433 reaction equation
CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.[C:16]([O:20][C:21](=[O:35])[NH:22][CH:23]1[C:30](=[O:31])[N:29]2[CH:25]([S:26][CH2:27][CH:28]2[C:32](=O)[NH2:33])[CH2:24]1)([CH3:19])([CH3:18])[CH3:17]>C1COCC1>[C:16]([O:20][C:21](=[O:35])[NH:22][CH:23]1[C:30](=[O:31])[N:29]2[CH:25]([S:26][CH2:27][CH:28]2[C:32]#[N:33])[CH2:24]1)([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 21015133HCID 21015133, compound

Product 1

HCID 68461440HCID 68461440, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Burgess reagent (0.8 g, 3.3 mmol) was added in portions to a solution of 5 (0.5 g, 1.58 mmol) in dry THF (20 mL) at room temperature, and was stirred overnight. The mixture was washed with water (20 mL), dried over Na2SO4, concentrated and purified by column chromatography on silica gel to produce compound 6 (0.2 g, 50%) 1H NMR (400 MHz, CDCl3) δ1.44 (s, 9 H), 2.08-2.11 (m, 1 H), 3.17-3.21 (m, 1H), 3.68 (d, 2 H), 4.50-4.60 (m, 1 H), 5.07 (s, 1 H), 5.14 (t, 1 H), 5.37 (t, 1 H).

Workup

  1. washThe mixture was washed with water (20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-2ddd8c036f034e709e7146c488da933b
Source dataset
uspto-grants-2010_08
Patent number
US07786163B2

Reaction notes

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