HCID 67148128, compound → 3-{3-[1-(5-Amino-2-tert-butoxycarbonylamino-pentanoyl)-pyrrolidin-2-ylmethyl]-benzofuran-2-yl}-propionic acid

HRID 1054012Notes

Reaction equation

HRID 1054012 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][CH:15]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:16]([N:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[CH2:23][C:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][C:25]=1[CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[O:17])=O)C1C=CC=CC=1>CO>[NH2:11][CH2:12][CH2:13][CH2:14][CH:15]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C:16]([N:18]1[CH2:22][CH2:21][CH2:20][CH:19]1[CH2:23][C:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][C:25]=1[CH2:33][CH2:34][C:35]([OH:37])=[O:36])=[O:17]

Participants

3

Reactant 1

HCID 67148128HCID 67148128, compound

Product 1

HCID 671488873-{3-[1-(5-Amino-2-tert-butoxycarbonylamino-pentanoyl)-pyrrolidin-2-ylmethyl]-benzofuran-2-yl}-propionic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the crude 54 (˜3 g, 4.8 mmol) in MeOH (30 mL) was charged with 10% Pd-on-carbon (˜1 g) and placed under an atmosphere of hydrogen gas (45 PSI). The reaction mixture was shaken using a Parr apparatus for 2 h. After removal of the catalyst by filtration over celite, the clarified filtrate was concentrated in vacuo. The crude residue was taken up in DCM and dried using anhydrous Na2SO4, filtered and concentrated to afford 2.3 g (quant.) of 55 as a foamy residue which was used without further purification. 1H NMR (CDCl3, 300 MHz) δ7.51 (m, 1H), 7.34-7.32 (m, 1H), 7.18-7.15 (m, 2H), 6.19 (m, 1H), 4.36 (m, 2H), 3.62-3.48 (m, 2H), 3.10-2.99 (m, 2H), 2.85-1.81 (m, 2H), 2.66-2.60 (m, 2H), 1.99-1.71 (m, 6H), 1.41 (s, 911) ppm. Mass spectrum, m/z 488 [M+H]+.

Workup

  1. customfor 2 h
  2. customAfter removal of the catalyst
  3. filtrationby filtration over celite
  4. concentrationthe clarified filtrate was concentrated in vacuo
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dd7defdb3148408baad13cbb303647d9
Source dataset
uspto-grants-2016_07
Patent number
US09394249B2

Reaction notes

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