Triphenylphosphine → HCID 20707085, compound

HRID 398512Notes

Reaction equation

HRID 398512 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrN1C(=O)CCC1=O.[CH:28]1([CH2:33][CH:34]([C:38]2[CH:43]=[CH:42][C:41]([S:44]([C:47]([F:50])([F:49])[F:48])(=[O:46])=[O:45])=[CH:40][CH:39]=2)[C:35]([OH:37])=O)[CH2:32][CH2:31][CH2:30][CH2:29]1.[NH2:51][C:52]1[S:53][CH:54]=[C:55]([CH2:57][C:58]([O:60][CH2:61][CH3:62])=[O:59])[N:56]=1>C(Cl)Cl>[CH2:61]([O:60][C:58](=[O:59])[CH2:57][C:55]1[N:56]=[C:52]([NH:51][C:35](=[O:37])[CH:34]([C:38]2[CH:39]=[CH:40][C:41]([S:44]([C:47]([F:49])([F:48])[F:50])(=[O:45])=[O:46])=[CH:42][CH:43]=2)[CH2:33][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32]2)[S:53][CH:54]=1)[CH3:62]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 223150923-Cyclopentyl-2-(4-trifluoromethanesulfonyl-phenyl)propionic acid

Product 1

HCID 20707085HCID 20707085, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of triphenylphosphine (97 mg, 0.371 mmol) in methylene chloride (1.5 mL) was cooled to 0° C. and then slowly treated with N-bromosuccinimide (66 mg, 0.371 mmol). The reaction mixture was stirred at 0° C. for 20 min and then treated with 3-cyclopentyl-2-(4-trifluoromethanesulfonyl-phenyl)propionic acid (100 mg, 0.285 mmol). The resulting reaction mixture was stirred at 0° C. for 10 min, allowed to warm to 25° C., and then treated with ethyl 2-amino-4-thiazoleacetate (123 mg, 0.657 mmol). The resulting reaction mixture was stirred at 25° C. for 3 d. The reaction mixture was then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 3/1 hexanes/ethyl acetate) afforded {2-[3-cyclopentyl-2-(4-trifluoromethanesulfonyl-phenyl)-propionyl-amino]-thiazol-4-yl}-acetic acid ethyl ester (107 mg, 72%) as a yellow foam: mp 48-51 ° C.; EI-HRMS m/e calcd for C22H25F3N2O5S2 (M+) 518.1157, found 518.1157.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at 0° C. for 10 min
  3. temperatureto warm to 25° C.
  4. customThe resulting reaction mixture
  5. stirringwas stirred at 25° C. for 3 d
  6. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-9f1fddef49ed4c1cae4cffc748ff622f
Source dataset
uspto-grants-2003_08
Patent number
US06610846B1

Reaction notes

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