Triethylamine → HCID 47451638, compound

HRID 1504938Notes

Reaction equation

HRID 1504938 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([CH3:14])([CH3:13])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.Cl.[CH3:28][NH:29][O:30][CH3:31].C(N(CC)CC)C>ClCCl.O>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]([C:10](=[O:12])[N:29]([O:30][CH3:31])[CH3:28])([CH3:14])[CH3:13])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine2×

Product 1

HCID 47451638HCID 47451638, compoundYield 38.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of afford 2-tert-butoxycarbonylamino-2-methyl-propionic acid (compound K; 60.0 g) and 1-ethyl-3(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC.HCl; 86.4 g) in dichloromethane (900 mL) was stirred at ambient temperature, then N,O-dimethyl hydroxylamine hydrochloride (35.3 g) and triethylamine (150 mL) were added. The resulting mixture was stirred at ambient temperature for 3 days. Water was added and most of volatiles were removed in vacuo. The residue was partitioned between DCM and aqueous NaHCO3. The organic layer was washed with 3M aqueous HCl, subsequently with brine before it was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography to give [1-(methoxy-methyl-carbamoyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester (compound L; 28.2 g) as a white solid sufficiently pure for the next step.

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature for 3 days
  2. customwere removed in vacuo
  3. customThe residue was partitioned between DCM and aqueous NaHCO3
  4. washThe organic layer was washed with 3M aqueous HCl, subsequently with brine before it
  5. dry with materialwas dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f145f99429a04695b0fd261c27a67d49
Source dataset
uspto-grants-2015_12
Patent number
US09216961B2

Reaction notes

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