Diisopropylethylamine → HCID 178419543, compound

HRID 2379496Notes

Reaction equation

HRID 2379496 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.[N:33]1([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:40][CH2:39][CH2:38][C@H:34]1[C:35](O)=[O:36]>CN(C=O)C>[N:33]1([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:40][CH2:39][CH2:38][C@H:34]1[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 81531Diisopropylethylamine3×HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 178419274HCID 178419274, compound

Product 1

HCID 178419543HCID 178419543, compoundYield 70%

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 4.71 mg (2.19 mmol) of Boc-L-Pro-OH in 50 ml of DMF is neutralized with 0.285 ml of DIEA. The two solutions are mixed and 970 mg of Bop are then added while the resulting mixture is kept at RT, with stirring, the pH being kept at between 7.0 and 8.0 throughout the reaction by the addition of small portions of DIEA. After one hour, the reaction is complete and the reaction mixture is evaporated to dryness under vacuum; the evaporation residue is taken up with an AcOEt/MeOH mixture and extracted with a 0.5 M aqueous solution of NaHCO3. The organic phase is dried over sodium sulfate, concentrated and precipitated in ether (MeOMe or EtOEt) to give 877 mg (yield: 70%) of the expected product.

Workup

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

Sources & evidence

ORD record
ord-fc6c15cbdf3c46e7bd71abab7541e0e4
Source dataset
uspto-grants-1994_11
Patent number
US05362851

Reaction notes

Loading…