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

HRID 1691584Notes

Reaction equation

HRID 1691584 reaction equation
[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=[O:4].O[N:14]1[C:19](=[O:20])[CH2:18][CH2:17][C:15]1=[O:16]>C(Cl)(Cl)Cl>[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([O:5][N:14]1[C:19](=[O:20])[CH2:18][CH2:17][C:15]1=[O:16])=[O:4]

Participants

4

Reactant 2

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 80170N-Hydroxysuccinimide

Product 1

HCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Boc-Gly-OH (1.54 g, 8.82 mmol) was put in a 500-mL eggplant flask and dissolved in distilled CHCl3. Then, DCU (2.18 g, 10.6 mmol) and HOSu (1.21 g, 10.6 mmol) were added thereto, and the stirring was started under cooling. After having been left standing overnight, the completion of the reaction was confirmed with TLC and the resultant was concentrated. After filtered, DCUrea was dissolved in AcOEt and the reprecipitated DCUrea was filtered. After that, the filtrate was concentrated and recrystallized with AcOEt-distilled Et2O twice, whereby Boc-Gly-OSu was obtained. The yield was 1.74 g (63.9%). 1H NMR (CDCl3, 300 MHz): 5.04 (1H, Boc-Gly NH); 4.27, 4.23 (2H, Gly αCH2); 2.79 (4H, OSu); 1.40 (9H, Boc t-Bu).

Workup

  1. temperatureunder cooling
  2. waitAfter having been left
  3. concentrationthe resultant was concentrated
  4. filtrationAfter filtered
  5. dissolutionDCUrea was dissolved in AcOEt
  6. filtrationthe reprecipitated DCUrea was filtered
  7. concentrationAfter that, the filtrate was concentrated
  8. customrecrystallized with AcOEt-
  9. distillationdistilled Et2O twice

Sources & evidence

ORD record
ord-6dc35b8e35c144f9abf6b48c88f7cb8c
Source dataset
uspto-grants-2012_04
Patent number
US08153759B2

Reaction notes

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