Trifluoroacetic acid → N-Isopropyl-4-methoxy-3-(3-methoxy-propoxy)-N-((3S*,4S*)-4-phenylamino methyl-pyrrolidin-3-ylmethyl)-benzamide

HRID 1158336Notes

Reaction equation

HRID 1158336 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([CH2:13][NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:10]([CH2:21][N:22]([CH:39]([CH3:41])[CH3:40])[C:23](=[O:38])[C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH2:33][CH2:34][CH2:35][O:36][CH3:37])[CH:25]=2)[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:39]([N:22]([CH2:21][C@H:10]1[C@H:11]([CH2:13][NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][NH:8][CH2:9]1)[C:23](=[O:38])[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH2:33][CH2:34][CH2:35][O:36][CH3:37])[CH:25]=1)([CH3:41])[CH3:40]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59512285(3R*,4R*)-3-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-4-phenylaminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 11851726N-Isopropyl-4-methoxy-3-(3-methoxy-propoxy)-N-((3S*,4S*)-4-phenylamino methyl-pyrrolidin-3-ylmethyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3R*,4R*)-3-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-4-phenylaminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (65 mg, 0.12 mmol) in 2 mL CH2Cl2, TFA (139 μL, 1.8 mmol) is added. The mixture is stirred 2 h at RT, and poured into a saturated solution of NaHCO3. The layers are separated, and the aqueous one is back-extracted twice with CH2Cl2. The combined organic extracts are dried over Na2SO4, filtered and concentrated. The crude material is purified by flash chromatography on an Isolute SPE Flash NH2 column (eluent: CH2Cl2/MeOH 100:0 to 97:3) to give the title product. TLC, Rf (SiO2—NH2, CH2Cl2/MeOH 95:5)=0.6. MS (LC-MS): 470.0 [M+H]+; tR (HPLC, Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 3.37 min.

Workup

  1. customThe layers are separated
  2. extractionthe aqueous one is back-extracted twice with CH2Cl2
  3. dry with materialThe combined organic extracts are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material is purified by flash chromatography on an Isolute SPE Flash NH2 column (eluent: CH2Cl2/MeOH 100:0 to 97:3)

Sources & evidence

ORD record
ord-637308d722534db9bd434a2ad6a25d66
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

Loading…