Methyl N-(triethylammoniosulfonyl)carbamate → HCID 59651100, compound

HRID 2426806Notes

Reaction equation

HRID 2426806 reaction equation
[CH2:1]([C@:8]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:28])[C:9](=O)[CH2:10][NH:11][C:12](=[O:26])[C:13]1[CH:18]=[C:17]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:22])=[O:21])[N:16]=[C:15]([Cl:25])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1(C)C=CC=CC=1>[Cl:25][C:15]1[CH:14]=[C:13]([C:12]2[O:26][C:9]([C@@:8]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:35])[CH3:34])([CH3:28])[CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:10][N:11]=2)[CH:18]=[C:17]([N:19]([CH3:24])[S:20]([CH3:23])(=[O:21])=[O:22])[N:16]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 86617874HCID 86617874, compound

Product 1

HCID 59651100HCID 59651100, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of tert-butyl (1R)-1-benzyl-3-({2-chloro-6-[methyl(methylsulfonyl)amino]isonicotinoyl}amino)-1-methyl-2-oxopropylcarbamate (0.190 g, 0.35 mmol) in 2 mL toluene was added Burgess reagent (0.504 g, 2.12 mmol). The reaction was microwaved at 130° C. for 30 min. The clear yellow, top layer of the reaction mixture was concentrated in vacuo and purified by normal phase chromatography (0->50% EtOAc/hexanes) to give tert-butyl (1R)-1-(2-{2-chloro-6-[methyl(methylsulfonyl)amino]pyridin-4-yl}-1,3-oxazol-5-yl)-1-methyl-2-phenylethylcarbamate. NMR (CDCl3, 400 MHz) 7.86 (s, 1H); 7.69 (s, 1H); 7.28 (m, 3H); 7.04 (m, 3H); 3.45 (s, 3H); 3.13 (m, 4H); 1.60 (s, 3H); 1.42 (s, 9H); LC/MS [M+H]+=521.

Workup

  1. customThe reaction was microwaved at 130° C. for 30 min
  2. concentrationThe clear yellow, top layer of the reaction mixture was concentrated in vacuo
  3. custompurified by normal phase chromatography (0->50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9e6574b3e1e24d4588183a34f9a9c52a
Source dataset
uspto-grants-2011_06
Patent number
US07968571B2

Reaction notes

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