Diisopropylethylamine → (S)-benzyl 2-(4-(tert-butoxycarbonylamino)phenylcarbamoyl)pyrrolidine-1-carboxylate

HRID 44452

Reaction equation

HRID 44452 reaction equation
[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[C:52]([O:56][C:57](=[O:66])[NH:58][C:59]1[CH:64]=[CH:63][C:62]([NH2:65])=[CH:61][CH:60]=1)([CH3:55])([CH3:54])[CH3:53]>CS(C)=O.O>[C:52]([O:56][C:57]([NH:58][C:59]1[CH:60]=[CH:61][C:62]([NH:65][C:13]([C@@H:12]2[CH2:16][CH2:17][CH2:18][N:11]2[C:1]([O:3][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2])=[O:15])=[CH:63][CH:64]=1)=[O:66])([CH3:55])([CH3:53])[CH3:54]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 101987Benzyloxycarbonyl-L-prolineHCID 688611tert-Butyl (4-aminophenyl)carbamateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 59396122(S)-benzyl 2-(4-(tert-butoxycarbonylamino)phenylcarbamoyl)pyrrolidine-1-carboxylateYield 70%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of Carbobenzyloxy-L-proline (0.20 g, 0.80 mmol) and HATU (0.32 g, 0.84 mmol) in DMSO (6 mL) was added diisopropylethylamine (0.42 mL, 2.41 mmol) followed by tert-buty-4-aminophenylcarbamate (0.175 g, 0.82 mmol). The solution was stirred at ambient temperature for two hours, then diluted with water and the solid product was filtered off and purified by combi-flash 12 g column, eluting with 0-20% ethyl acetate in dichloromethane to give a solid (0.245 g, 70%).

Workup

  1. filtrationthe solid product was filtered off
  2. custompurified by combi-flash 12 g column
  3. washeluting with 0-20% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-4a825562167a45caa179f859a95ce40d
Source dataset
uspto-grants-2013_09
Patent number
US08541424B2

Linked notes

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