Trifluoroacetic acid → 3(S)-(6-Methoxy-pyridin-3-yl)-3-[2-oxo-3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)-propyl]-2,3-dihydro-imidazol-1-yl}-propionic acid

HRID 993247Notes

Reaction equation

HRID 993247 reaction equation
C([O:5][C:6](=[O:37])[CH2:7][C@@H:8]([C:29]1[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=1)[N:9]1[CH:13]=[CH:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]3[CH2:26][CH2:25][CH2:24][CH2:23][NH:22][C:21]=3[N:27]=2)[C:10]1=[O:28])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:36][O:35][C:32]1[N:31]=[CH:30][C:29]([C@@H:8]([N:9]2[CH:13]=[CH:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]4[CH2:26][CH2:25][CH2:24][CH2:23][NH:22][C:21]=4[N:27]=3)[C:10]2=[O:28])[CH2:7][C:6]([OH:37])=[O:5])=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 701276213(S)-(6-Methoxy-pyridin-3-yl)-3-{2-oxo-3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)-propyl]-2,3-dihydro-imidazol-1-yl}-propionic acid tert-butyl ester

Product 1

HCID 599164503(S)-(6-Methoxy-pyridin-3-yl)-3-[2-oxo-3-[3-(6,7,8,9-tetrahydro-5H-pyrido[2,3-b]azepin-2-yl)-propyl]-2,3-dihydro-imidazol-1-yl}-propionic acidYield 79.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-7 (0.85 g, 1.67 mmol) in dichloromethane (10 mL) was added anhydrous TFA (5 mL). After 4 hours, the mixture was concentrated, diluted with toluene, and re-concentrated. The residue was chromatographed on silica gel (15:10:1:1 to 15:10:1:1 EtOAc/EtOH(NH4OH/H2O) to give 600 mg of 3-8 as a white solid.

Workup

  1. concentrationthe mixture was concentrated
  2. additiondiluted with toluene
  3. concentrationre-concentrated
  4. customThe residue was chromatographed on silica gel (15:10:1:1 to 15:10:1:1 EtOAc/EtOH(NH4OH/H2O)

Sources & evidence

ORD record
ord-ab7a5c04e3124a7fa0985ef3585ddb34
Source dataset
uspto-grants-2002_10
Patent number
US06472403B2

Reaction notes

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