Methyl iodide → HCID 178501506, compound

HRID 75764Notes

Reaction equation

HRID 75764 reaction equation
[Na].[CH3:2][O:3][C:4](=[O:34])[C@@H:5]([NH:9][C:10]([C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]3[S:25][C:26]4[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:27]=4[N:28]=3)=[CH:19][CH:18]=2)[CH:13]=1)=S)[CH:6]([CH3:8])[CH3:7].IC.Cl.[NH2:38][OH:39].C([O-])(O)=O.[Na+]>CO>[CH3:2][O:3][C:4](=[O:34])[C@@H:5]([NH:9][C:10]([C:12]1[O:16][N:15]=[C:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23][C:24]3[S:25][C:26]4[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:27]=4[N:28]=3)=[CH:19][CH:18]=2)[CH:13]=1)=[N:38][OH:39])[CH:6]([CH3:8])[CH3:7]

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 46181830(S)-2-({3-[4-(6-fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carbothioyl}-amino)3-methyl-butyric acid methyl ester

Product 1

HCID 178501506HCID 178501506, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of freshly cleaned sodium pieces (0.043 g; 1.86 matom) in dry MeOH (30 ml) was added (S)-2-({3-[4-(6-fluoro-benzothiazol-2-ylamino)-phenyl]-isoxazole-5-carbothioyl}-amino)3-methyl-butyric acid methyl ester (0.9 g; 1.86 mmol) under stirring followed by iodomethane (0.23 ml; 3.72 mmol). The stirring was continued for 2 hours at room temperature. Hydroxylamine hydrochloride (0.284 g; 4.09 mmol) was added to this solution followed by NaHCO3 (0.343 g; 4.09 mmol) and the resulting reaction mixture was refluxed for 3 hours. The solid thus obtained was filtered, dried and purified by flash chromatography over silica gel with 5% MeOH in chloroform to obtain 0.61 g (68%) of the title compound. Mass (ES−): 482 (M−1); IR (KBr): 3384, 3196, 2963, 1737, 1642, 1611, 1546 (br), 1462 (br); 1H NMR (DMSO-d6) δ: 0.89, 0.94 (2×d, 6H), 2.08 (m, 1H), 3.65 (s, 3H), 3.99 (m, 1H), 5.85 (d, 1H), 7.20 (m, 1H), 7.29 (s, 1H), 7.66 (m, 1H), 7.79 (m, 1H), 7.93 (s, 4H), 10.78 (s, 1H); 10.85 (s, 1H).

Workup

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 3 hours
  3. customThe solid thus obtained
  4. filtrationwas filtered
  5. customdried
  6. custompurified by flash chromatography over silica gel with 5% MeOH in chloroform

Sources & evidence

ORD record
ord-0a3a1299eb51407fa2f94d490aed4ba9
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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