HCID 16666560, compound → HCID 67006887, compound

HRID 562581Notes

Reaction equation

HRID 562581 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([CH:39]=[CH:40][CH:41]=1)[C:6]([NH:8][CH2:9][C:10]([NH:12][C@@H:13]1[CH2:17][CH2:16][N:15]([CH:18]2[CH2:22][CH2:21][N:20]([C:23]3[CH:38]=[CH:37][C:26]([C:27]([O:29]CC4C=CC=CC=4)=[O:28])=[CH:25][CH:24]=3)[CH2:19]2)[CH2:14]1)=[O:11])=[O:7].[H][H]>CO.[Pd]>[F:43][C:2]([F:1])([F:42])[C:3]1[CH:4]=[C:5]([CH:39]=[CH:40][CH:41]=1)[C:6]([NH:8][CH2:9][C:10]([NH:12][C@@H:13]1[CH2:17][CH2:16][N:15]([CH:18]2[CH2:22][CH2:21][N:20]([C:23]3[CH:38]=[CH:37][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=3)[CH2:19]2)[CH2:14]1)=[O:11])=[O:7]

Participants

5

Reactant 2

HCID 16666560HCID 16666560, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67006887HCID 67006887, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

In a round-bottom flask, a solution of benzyl 4-{(3R)-3-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]-1,3′-bipyrrolidin-1′-yl}benzoate (258 mg, 0.43 mmol) in methanol (400 μL) and Palladium (10%) on Carbon (50 mg) was purged with hydrogen gas for two minutes; the reaction was then subjected to 1 atmosphere of hydrogen gas for two hours. The flask was purged with Argon, then the mixture was filtered and concentrated to afford 4-{(3R)-3-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]-1,3′-bipyrrolidin-1′-yl}benzoic acid (197 mg, 91%) as an off-white solid.

Workup

  1. customThe flask was purged with Argon
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3205167ccbca4a88ab13f56b0b221596
Source dataset
uspto-grants-2011_11
Patent number
US08067415B2

Reaction notes

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