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

HRID 528674

Reaction equation

HRID 528674 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[N:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=[O:20].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:4]([O:3][C:1]([NH:8][CH2:9][C:10]([O:12][N:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=[O:20])=[O:11])=[O:2])([CH3:6])([CH3:7])[CH3:5]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 80170N-Hydroxysuccinimide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Boc-glycine (7.31 g, 41.7 mmol) was dissolved in 100 mL of DCM and to the cooled (15° C.) solution N-hydroxysuccinimide (5.28 g, 45.9 mmol) was added. N,N′-dicyclohexylcarbodiimide (9.47 g, 45.9 mmol) was added to the formed suspension under vigorous stirring. After a few seconds, a cloudy white suspension formed, the mixture was allowed to reach room temperature and stirred for 1 h. It was subsequently filtrated over celite, washed with 50 mL saturated sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo to yield a crystalline powder. Yield: 7.02 g, 61.8%

Workup

  1. additionwas added
  2. waitAfter a few seconds
  3. customa cloudy white suspension formed
  4. customto reach room temperature
  5. filtrationIt was subsequently filtrated over celite
  6. washwashed with 50 mL saturated sodium bicarbonate
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto yield a crystalline powder

Sources & evidence

ORD record
ord-5de66e3e0b704fb984cf6ce0ec846149
Source dataset
uspto-grants-2016_05
Patent number
US09346814B2

Linked notes

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