4-Methylmorpholine → tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate

HRID 254833Notes

Reaction equation

HRID 254833 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:14][NH:15][O:16][CH3:17].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[CH3:17][O:16][N:15]([CH3:14])[C:10](=[O:12])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 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 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 2-(tert-butoxycarbonylamino)acetic acid (800 mg, 4.57 mmol), N,O-dimethylhydroxylamine hydrochloride (535 mg, 5.48 mmol), EDCI (1.05 g, 5.48 mmol), HOBt (740 mg, 5.48 mmol) in DCM (25 mL) was added NMM (2.77 g, 27.42 mmol) at rt. The reaction mixture was stirred overnight. After the reaction was completed, DCM was evaporated in vacuo. The residue was dissolved in MeOH, filtered through a syringe filter, and then purified by reverse-phase prep HPLC to provide the desired product (705 mg, 71%) as white solid

Workup

  1. customDCM was evaporated in vacuo
  2. dissolutionThe residue was dissolved in MeOH
  3. filtrationfiltered through a syringe
  4. filtrationfilter
  5. custompurified by reverse-phase prep HPLC

Sources & evidence

ORD record
ord-02f77e9a8e5c4c268fbfa94eb9ad0b5a
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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