1,1,1-Trifluoro-N-phenylmethanesulfonamide → 2-[(3-Hydroxy-5-trifluoromethanesulfonyloxy-pyridine-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester

HRID 2188525Notes

Reaction equation

HRID 2188525 reaction equation
C(N(C(C)C)CC)(C)C.C1(N[S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])C=CC=CC=1.[CH3:24][O:25][C:26](=[O:41])[C:27]([NH:30][C:31]([C:33]1[C:38]([OH:39])=[CH:37][C:36]([OH:40])=[CH:35][N:34]=1)=[O:32])([CH3:29])[CH3:28]>CO>[CH3:24][O:25][C:26](=[O:41])[C:27]([NH:30][C:31]([C:33]1[C:38]([OH:39])=[CH:37][C:36]([O:40][S:17]([C:20]([F:21])([F:22])[F:23])(=[O:18])=[O:19])=[CH:35][N:34]=1)=[O:32])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 680121,1,1-Trifluoro-N-phenylmethanesulfonamideHCID 81531DiisopropylethylamineHCID 595130812-[(3,5-Dihydroxy-pyridine-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester

Product 1

HCID 595130782-[(3-Hydroxy-5-trifluoromethanesulfonyloxy-pyridine-2-carbonyl)-amino]-2-methyl-propionic acid methyl esterYield 36%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution in 2-[(3,5-dihydroxy-pyridine-2-carbonyl)-amino]-2-methyl-propionic acid methyl ester, 18, (0.312 g, 1.23 mmol) in MeOH (10 mL) containing diisopropylethylamine (0.214 mL, 1.23 mmol) at 0° C. under N2 is added N-phenyltrifluoromethanesulfonamide (0.439 g, 1.23 mmol). The reaction is warmed slowly to room temperature and stirred for 40 hours. The solvent is removed under reduced pressure and the crude oil which remains is purified over silica (EtOAc:heptane 1:9) to afford 0.170 g (36% yield) of the desired compound as a yellow oil. 1H NMR (250 MHz, MeOD) δ ppm 8.85 (1H, br s), 8.19 (1H, d, J=2.4 Hz), 7.46 (1H, d, J=2.3 Hz), 3.74 (3H, s), 1.63 (6H, s). HPLC-MS: m/z 387 [M+H]+.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe crude oil which remains is purified over silica (EtOAc:heptane 1:9)

Sources & evidence

ORD record
ord-50ab337f0aad4ddfbf0bc2af7aa83092
Source dataset
uspto-grants-2012_12
Patent number
US08323671B2

Reaction notes

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