N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester →

HRID 1157359Notes

Reaction equation

HRID 1157359 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([O-:4])=[O:3].C(N(C(C)C)CC)(C)C.[NH:22](C(OC(C)(C)C)=O)[CH2:23][C:24]([O:26]N1C(=O)CCC1=O)=[O:25]>ClCCl>[NH2:22][CH2:23][CH:24]([OH:26])=[O:25].[ClH:1].[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH-:10])=[CH:11][CH:12]=1)([O-:4])=[O:3]

Participants

4

Reactant 3

HCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 81531DiisopropylethylamineHCID 112524674-Nitrobenzylamine hydrochloride

Product 0

No Product data yet.

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Nitrobenzylamine hydrochloride (1 g; 5.3 mmol) and diisopropylethylamine (1.8 ml; 10.6 mmol) were dissolved in 70 ml of dichloromethane at RT. BOC-Gly-OSu (1.44 g; 5.3 mmol) was added and the solution was stirred at RT overnight. After evaporating the solvent in a rotary evaporator, the residue was taken up in 50 ml of ethyl acetate and extracted in each case 2× with 5% KHSO4, 5% NaHCO3 and distilled water. The organic phase was dried over Na2SO4, the solvent was evaporated and toluene was then added and evaporated in a rotary evaporator. The resultant oil was dissolved, without further work-up, directly in 15 ml of 4M HCl/dioxane and stirred at RT. After a short time, the product starts to precipitate. After 1 h, the solvent was evaporated, the solid was suspended in 100 ml of ethyl acetate, filtered off and washed with petroleum ether. The white solid was dried under vacuum.

Workup

  1. customAfter evaporating the solvent
  2. customin a rotary evaporator
  3. extractionextracted in each case 2× with 5% KHSO4, 5% NaHCO3
  4. distillationdistilled water
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customthe solvent was evaporated
  7. additiontoluene was then added
  8. customevaporated in a rotary evaporator
  9. dissolutionThe resultant oil was dissolved, without further work-up, directly in 15 ml of 4M HCl/dioxane
  10. stirringstirred at RT
  11. customto precipitate
  12. waitAfter 1 h
  13. customthe solvent was evaporated
  14. filtrationfiltered off
  15. washwashed with petroleum ether
  16. customThe white solid was dried under vacuum

Sources & evidence

ORD record
ord-553e4897f1894601844831a0754ac605
Source dataset
uspto-grants-2010_10
Patent number
US07807681B2

Reaction notes

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