N-(tert-butoxycarbonyl)glycine → Tert-butyl [(4-bromophenyl)(ethyl)aminocarbonylmethyl]carbamate

HRID 1465454Notes

Reaction equation

HRID 1465454 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5](NCC)=[CH:4][CH:3]=1.[C:11]([NH:18][CH2:19][C:20]([OH:22])=O)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].Cl.[CH2:24]([N:26]=C=NCCCN(C)C)[CH3:25].C(=O)([O-])O.[Na+]>N1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:19]([NH:18][C:11](=[O:12])[O:13][C:14]([CH3:15])([CH3:16])[CH3:17])[C:20]([NH:26][CH2:24][CH3:25])=[O:22])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 117456564-bromo-N-ethylaniline

Product 1

HCID 86651843Tert-butyl [(4-bromophenyl)(ethyl)aminocarbonylmethyl]carbamateYield 99%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromo-N-ethylaniline (1.28 g, 6.4 mmol), N-Boc-glycine (1.57 g, 9.0 mmol) in pyridine (10 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.47 g, 7.7 mmol) at 0° C. The reaction mixture was stirred at room temperature for 4 hrs. The reaction mixture was poured into a mixture of diluted aqueous sodium hydrogen carbonate solution and ethyl acetate. The mixture was stirred, stood still and partitioned. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give tert-butyl [(4-bromophenyl)(ethyl)aminocarbonylmethyl]carbamate (2.255 g, yield 99%) as a yellow solid.

Workup

  1. stirringThe mixture was stirred
  2. custompartitioned
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-25a144044dc44926b0ad03b5e4a7d73f
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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