Methyl N-(triethylammoniosulfonyl)carbamate → HCID 131727919, compound

HRID 2242654Notes

Reaction equation

HRID 2242654 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C@H:8]([C:27]([N:29]1[CH2:33][CH2:32][C:31]([F:35])([F:34])[CH2:30]1)=[O:28])[C@H:9]([CH:11]1[CH2:16][CH2:15][C:14](O)([C:17]2[N:22]3[N:23]=[CH:24][N:25]=[C:21]3[CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)[CH3:10])([CH3:4])([CH3:3])[CH3:2].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[C:1]([O:5][C:6](=[O:36])[NH:7][C@H:8]([C:27]([N:29]1[CH2:33][CH2:32][C:31]([F:35])([F:34])[CH2:30]1)=[O:28])[C@H:9]([CH:11]1[CH2:16][CH2:15][C:14]([C:17]2[N:22]3[N:23]=[CH:24][N:25]=[C:21]3[CH:20]=[CH:19][CH:18]=2)=[CH:13][CH2:12]1)[CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 131727920HCID 131727920, compound

Product 1

HCID 131727919HCID 131727919, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound prepared in Step A (0.13 g, 0.26 mmol) in THF (5 mL) was added Burgess reagent (0.19 g, 0.78 mmol). After 1 h at ambient temperature, the reaction mixture was concentrated to 1 mL in vacuo. The remaining solution was added to saturated aqueous sodium bicarbonate and the resulting mixture was extracted with dichloromethane. The combined organic layers were dried (anhydrous sodium sulfate) and concentrated in vacuo to give the title compound. LC/MS 490.4 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated to 1 mL in vacuo
  2. additionThe remaining solution was added to saturated aqueous sodium bicarbonate
  3. extractionthe resulting mixture was extracted with dichloromethane
  4. dry with materialThe combined organic layers were dried (anhydrous sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5759af0ce19e43af80ccf191944b656c
Source dataset
uspto-grants-2010_03
Patent number
US07671073B2

Reaction notes

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