Trimethylphosphine → (S)-2-[[1-(2-aminoethyl)cyclopentanecarbonyl]amino]-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid

HRID 393447Notes

Reaction equation

HRID 393447 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1([C:11]([NH:13][C@H:14]([C:33]([OH:35])=[O:34])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]3[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:32])=[O:24])=[CH:18][CH:17]=2)=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[N+]=[N-].CP(C)C>C1COCC1>[NH2:1][CH2:4][CH2:5][C:6]1([C:11]([NH:13][C@H:14]([C:33]([OH:35])=[O:34])[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]3[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:32])=[O:24])=[CH:18][CH:17]=2)=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 68983TrimethylphosphineHCID 44461305HCID 44461305, compound

Product 1

HCID 10174347(S)-2-[[1-(2-aminoethyl)cyclopentanecarbonyl]amino]-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of N-[[1-(2-azidoethyl)cyclopentyl]carbonyl]-4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine on Wang resin (9.33 mmol, 13.43 g, 0.695 mmol per g) in THF (60 mL) was added a solution of 1.0 M trimethylphosphine in THF (37.3 mmol, 37.3 mL) at 0° C. The mixture was allowed to warm to room temperature and stir for 4 h at which time a Kaiser test was possitve for amine. The resin was filtered and was washed with DMF (4×20 mL), dichloromethane (4×10 mL), isopropanol (4×10 mL), DMF (2×20 mL) and dichloromethane (2×20 mL), respectively. After drying under high vacuum, 13.43 g of N-[[1-(2-aminoethyl)cyclopentyl]carbonyl]-4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine on Wang resin was obtained.

Workup

  1. filtrationThe resin was filtered
  2. washwas washed with DMF (4×20 mL), dichloromethane (4×10 mL), isopropanol (4×10 mL), DMF (2×20 mL) and dichloromethane (2×20 mL)
  3. dry with materialAfter drying under high vacuum, 13.43 g of N-[[1-(2-aminoethyl)cyclopentyl]carbonyl]-4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine on Wang resin
  4. customwas obtained

Sources & evidence

ORD record
ord-1b0010c5ecaa43c9b1eb3cc9da7f3d28
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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