N-(tert-butoxycarbonyl)glycine → HCID 178419547, compound

HRID 483641Notes

Reaction equation

HRID 483641 reaction equation
[NH2:1][C@H:2]([C:10]([NH:12][C:13]1[CH:21]=[CH:20][C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=1)=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[BrH:22].Br.CCN(C(C)C)C(C)C.[NH:33]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][C:35](O)=[O:36]>CN(C=O)C>[NH:33]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:34][C:35]([NH:1][C@H:2]([C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([N+:17]([O-:19])=[O:18])=[CH:20][CH:21]=1)=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9])=[O:36].[BrH:22]

Participants

5

Reactant 3

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531Diisopropylethylamine3×HCID 178419274HCID 178419274, compound

Product 1

HCID 178419547HCID 178419547, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1 g (2.19 mmol) of H-L-Arg-pNA.2HBr is dissolved in 10 ml of DMF, and 0.854 ml (6.57 mmol) of DIEA is then added. In another vessel, a solution of 384 mg (2.19 mmol) of Boc-Gly-OH in 5 ml of DMF is neutralized with 0.285 ml of DIEA. The two solutions obtained in this way are mixed and 970 mg of Bop are added to the resulting medium, the latter being kept at RT; also, the pH is kept at a value of between 7 and 8 by the addition of small portions of DIEA throughout the reaction. After one hour, the reaction has completely finished and the reaction medium is evaporated to dryness under vacuum; the evaporation residue is taken up with an AcOEt/MeOH mixture and extracted with a 0.5M aqueous solution of NaHCO3. The organic phase is dried over sodium sulfate, concentrated under vacuum and then precipitated in ether (MeOMe or EtOEt) to give 874 mg (yield: 75%) of the expected product.

Workup

  1. customThe two solutions obtained in this way
  2. additionare mixed
  3. addition970 mg of Bop are added to the resulting medium
  4. custombeing kept at RT
  5. customthe reaction medium is evaporated to dryness under vacuum
  6. extractionextracted with a 0.5M aqueous solution of NaHCO3
  7. dry with materialThe organic phase is dried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. customprecipitated in ether (MeOMe or EtOEt)

Sources & evidence

ORD record
ord-1bf4bf2bcf0e42e8a61b46ad7cf983e1
Source dataset
uspto-grants-1993_07
Patent number
US05225532

Reaction notes

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