N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester → HCID 178453838, compound

HRID 1731591Notes

Reaction equation

HRID 1731591 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[NH:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14][C:15](ON1C(=O)CCC1=O)=[O:16]>CN(C=O)C>[NH:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14][C:15]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9])=[O:16]

Participants

4

Reactant 2

HCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 178418600HCID 178418600, compound

Product 1

HCID 178453838HCID 178453838, compoundYield 151.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

109.2 Grams (0.27 mol) of H-Arg-CHA.2HCl was dissolved in 290 ml of DMF and then 70.2 ml (0.54 mol) of NEM was added thereto, followed by further addition of 81.7 g (0.3 mol) of BOC-Gly-OSu at 0° to 5° C. and the reaction was carried out at room temperature for 18 hours. After the reaction was completed, the DMF was removed by evaporation under a reduced pressure and the residue was dissolved in 500 ml of MeOH and reprecipitated in 8 liters of AcOEt. The crystals precipitated were collected by filtration and dried to obtain 135.8 g (100%) of BOC-Gly-Arg-CHA.HCl. Rf1 =0.46. Melting point: 214.5° C. (decomposed). [α]D20 -22 (C=1, MeOH)

Workup

  1. addition70.2 ml (0.54 mol) of NEM was added
  2. customthe DMF was removed by evaporation under a reduced pressure
  3. dissolutionthe residue was dissolved in 500 ml of MeOH
  4. customreprecipitated in 8 liters of AcOEt
  5. customThe crystals precipitated
  6. filtrationwere collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-503226a451cb476eaaa56ef60acd923e
Source dataset
uspto-grants-1986_11
Patent number
US04622389

Reaction notes

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