Hydrochloric Acid → tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

HRID 2042925Notes

Reaction equation

HRID 2042925 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH3:14][NH:15][O:16][CH3:17].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.Cl>C(Cl)Cl>[CH3:17][O:16][N:15]([CH3:14])[C:10](=[O:12])[CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 4428209tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamateYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of N-Boc-glycine 44 (10.0 g, 57.1 mmol), N,O-dimethylhydroxylamine hydrochloride (6.68 g, 68.5 mmol), EDCI (13.1 g, 68.5 mmol), and HOBt (9.26 g, 68.5 mmol) in CH2Cl2 (200 mL) was added NMM (31.4 mL, 285 mmol). The resulting mixture was stirred at room temperature for 15 h. The reaction mixture was poured into 1.0 M HCl solution, and extracted with EtOAc. The organic phase was washed with a saturated NaHCO3 solution and brine, and then dried over anhydrous MgSO4. After evaporation of solvent, the residue was triturated with hexanes (100 mL) to provide the Weinreb amide 45 (10.2 g, 82%) as white solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with a saturated NaHCO3 solution and brine
  3. dry with materialdried over anhydrous MgSO4
  4. customAfter evaporation of solvent
  5. customthe residue was triturated with hexanes (100 mL)

Sources & evidence

ORD record
ord-721ff9bfb29a45ed8c5a6862f8f6f443
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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