Methylamine → Benzyl ((2R,3S)-2-((4-((methylamino)methyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate

HRID 708533Notes

Reaction equation

HRID 708533 reaction equation
[CH:1]([C:3]1[CH:7]=[N:6][N:5]([CH2:8][C@@H:9]2[C@H:12]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11](=[O:24])[NH:10]2)[N:4]=1)=O.[CH3:25][NH2:26].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:25][NH:26][CH2:1][C:3]1[CH:7]=[N:6][N:5]([CH2:8][C@@H:9]2[C@H:12]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11](=[O:24])[NH:10]2)[N:4]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 131733826Benzyl((2R,3S)-2-((4-formyl-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate

Product 1

HCID 131733845Benzyl ((2R,3S)-2-((4-((methylamino)methyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of benzyl ((2R,3S)-2-((4-formyl-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate (340 mg, 1.03 mmol) in DCE (10 mL) was added MeNH2 (1032 μl, 2.065 mmol). After stirring for 1 h at rt, sodium triacetoxyborohydride (438 mg, 2.07 mmol) was added and the mixture was stirred overnight, whereupon it was quenched with saturtaed NaHCO3 (aq) at 0° C. and extracted with EtOAc (2×). The organic extracts were combined, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The resulting crude material (assumed quantitative) was used as such in step 4.

Workup

  1. stirringthe mixture was stirred overnight, whereupon it
  2. customwas quenched with saturtaed NaHCO3 (aq) at 0° C.
  3. extractionextracted with EtOAc (2×)
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c335ce0c2c9c451fa0caaa26ab06838e
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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