114873-01-7 → HCID 178501456, compound

HRID 2299170Notes

Reaction equation

HRID 2299170 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:11]([OH:13])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[CH:5]=1.[NH2:21][C@H:22]([C:33]([O:35][CH3:36])=[O:34])[CH2:23][CH2:24][CH2:25][NH:26][C:27](=[NH:32])[NH:28][N+:29]([O-:31])=[O:30].Cl.OC1C2N=NNC=2C=CC=1.Cl.CNC(N=C=NCC)CCNC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[NH2:1][C@H:2]([C:11]([NH:21][C@H:22]([C:33]([O:35][CH3:36])=[O:34])[CH2:23][CH2:24][CH2:25][NH:26][C:27](=[NH:32])[NH:28][N+:29]([O-:31])=[O:30])=[O:13])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[CH:5]=1

Participants

7

Reactant 4

HCID 2734492114873-01-7HCID 230638721,3-Dimethylaminopropyl-3-ethylcarbodiimide hydrochlorideHCID 178418300HCID 178418300, compoundHCID 178501503HCID 178501503, compound

Product 1

HCID 178501456HCID 178501456, compoundYield 105.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2.00 gm of BOC-3-F-Phe-OH (7.06 mmol), 2.09 gm of Arg(NO2)-OMe HCl (7.77 mmol), 1.05 gm of hydroxybenzotriazole and 2.58 gm of 4-dimethylaminopyridine in 50 mL of methylene chloride was added 1.5 gm of 1,3-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride. After stirring for 15 hours 100 mL more methylene chloride was added to the reaction, and it was washed three times with 100 mL portions of 10% aqueous hydrochloric acid solution, twice with 100 mL of 50% saturated sodium bicarbonate solution, once with 100 mL of saturated brine, dried over anhydrous magnesium sulfate, filtered, and the solvent removed under reduced pressure to yield 2.96 gm of product. This was dissolved in 100 mL of 10% trifluoroacetic acid in methylene chloride, stirred for 2 hours, and the solvent removed rapidly under reduced pressure. The material was triturated with diethyl ether and dried under high vacuum to yield product.

Workup

  1. additionwas added to the reaction, and it
  2. washwas washed three times with 100 mL portions of 10% aqueous hydrochloric acid solution
  3. dry with materialtwice with 100 mL of 50% saturated sodium bicarbonate solution, once with 100 mL of saturated brine, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-1a65b92ad45944df8b58705fd48c19f0
Source dataset
uspto-grants-2002_12
Patent number
US06495589B2

Reaction notes

Loading…