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

HRID 1582652Notes

Reaction equation

HRID 1582652 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].C(N1CCOCC1)C.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH3:14][N:15]([O:16][CH3:17])[C:10](=[O:12])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

Participants

6

Reactant 4

HCID 7525EthylmorpholineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 4428209tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamateYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution containing 18.8 g of N-tert.-butoxycarbonylglycine in 180 ml of anhydrous dichloromethane was stirred under nitrogen and cooled at 0-5° C. while 11.5 g of N,O-dimethylhydroxylamine hydrochloride, 27.1 g of N-ethylmorpholine and 22.5 g of N-ethyl-N′-(3-dimethylaminopropyl)carbodiimide hydrochloride were added. The mixture was allowed to warm slowly to room temperature and stirred for 16 h. The mixture was washed twice with 150 ml of 1M hydrochloric acid, and 150 ml of saturated sodium hydrogen carbonate then dried over anhydrous sodium sulphate, filtered and evaporated to give 22.5 g of N-tert.-butoxycarbonylglycine N-methyl-N-methoxyamide as a white solid which was used without further purification.

Workup

  1. additionwere added
  2. stirringstirred for 16 h
  3. washThe mixture was washed twice with 150 ml of 1M hydrochloric acid, and 150 ml of saturated sodium hydrogen carbonate
  4. dry with materialthen dried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1298a2a79f9f4fe8870d1248dc84bf3f
Source dataset
uspto-grants-2004_05
Patent number
US06737429B2

Reaction notes

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