Methanamine, N-methoxy-, hydrochloride (1:1) → Tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylisothiazol-5-ylcarbamate

HRID 1772346Notes

Reaction equation

HRID 1772346 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][N:12]=[C:11]([CH3:14])[C:10]=1[C:15]([OH:17])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN([C:21]([O:25][N:26]1N=NC2C=CC=N[C:27]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.CNOC>C1COCC1>[CH3:21][O:25][N:26]([CH3:27])[C:15]([C:10]1[C:11]([CH3:14])=[N:12][S:13][C:9]=1[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:17]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 608689985-{[(Tert-butoxy)carbonyl]amino}-3-methyl-1,2-thiazole-4-carboxylic acid

Product 1

HCID 86706923Tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylisothiazol-5-ylcarbamateYield 65.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(tert-butoxycarbonylamino)-3-methylisothiazole-4-carboxylic acid (2.10 g, 8.13 mmol) in THF (45 mL) at 0° C. were added HATU (3.70 g, 9.76 mmol) and Hunig's base (3.15 g, 24.4 mmol). After a period of 5 min, N,O-dimethylhydroxylamine hydrochloride (1.03 g, 10.6 mmol) was added to the previous mixture. After a period of 1.5 h at rt, the resulting mixture was evaporated under reduced pressure and purified by flash chromatography (EtOAc/hexane 1:9 to 10:0) to give tert-butyl 4-(methoxy(methyl)carbamoyl)-3-methylisothiazol-5-ylcarbamate as an oil (1.60 g). LRMS (M+H)+: 302 m/z.

Workup

  1. waitAfter a period of 1.5 h at rt
  2. customthe resulting mixture was evaporated under reduced pressure
  3. custompurified by flash chromatography (EtOAc/hexane 1:9 to 10:0)

Sources & evidence

ORD record
ord-f2f96cd76e88422e958e72a8cbfa8514
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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