(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid → HCID 178451945, compound

HRID 1906135Notes

Reaction equation

HRID 1906135 reaction equation
[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:24]([OH:26])=[O:25])[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:23])[NH:19][N+:20]([O-:22])=[O:21])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:27]1([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:34][CH2:33][CH2:32][C@@H:28]1[C:29](O)=[O:30]>CN(C=O)C.CCOC(C)=O>[N:27]1([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:34][CH2:33][CH2:32][C@@H:28]1[C:29]([NH:1][C@H:2]([C:10]([NH:12][C@H:13]([C:24]([OH:26])=[O:25])[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:23])[NH:19][N+:20]([O-:22])=[O:21])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:30]

Participants

5

Reactant 2

HCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidHCID 178512177HCID 178512177, compound

Product 1

HCID 178451945HCID 178451945, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Next, 1.34 g (2.5 m moles) of H-Phe-Arg(NO2)-CHA was dissolved in 10 ml of 0.75N-NEM/DMF, to this solution was added 0.84 g (2.5 m moles) of BOC-D-Pro-SDP at 0° to 5° C. and reacted at room temperature for 18 hours. After the reaction was completed, the reaction mixture was diluted with 150 ml of AcOEt, and washed 4 times with 50 ml of cold 5% hydrochloric acid, and washed twice with 50 ml of an aqueous solution saturated with sodium chloride, then decolored and dried with activated carbon and anhydrous magnesium sulfate. After drying, magnesium sulfate and activated carbon were removed by filtration, and the solvent was removed from the filtrate by evaporation under reduced pressure to obtain crude product of BOC-D-Pro-Phe-Arg(NO2)-CHA, recrystallized from AcOEt to obtain 1.2 g (85.9%) of BOC-D-Pro-Phe-Arg(NO2)-CHA.

Workup

  1. customreacted at room temperature for 18 hours
  2. washwashed 4 times with 50 ml of cold 5% hydrochloric acid
  3. washwashed twice with 50 ml of an aqueous solution saturated with sodium chloride
  4. dry with materialdried with activated carbon and anhydrous magnesium sulfate
  5. customAfter drying
  6. custommagnesium sulfate and activated carbon were removed by filtration
  7. customthe solvent was removed from the filtrate by evaporation under reduced pressure

Sources & evidence

ORD record
ord-432e012f709741a2b35b89030e23ef4f
Source dataset
uspto-grants-1987_03
Patent number
US04650753

Reaction notes

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