HCID 45101529, compound → HCID 11679210, compound

HRID 2223143Notes

Reaction equation

HRID 2223143 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7][N:8]([C@@H:23]([C:25]1[N:26]([C:36]2[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]([F:47])([F:46])[F:45])=[CH:38][CH:37]=2)[C:27](=[O:35])[C:28]2[CH:34]=[CH:33][CH:32]=[N:31][C:29]=2[N:30]=1)[CH3:24])[C:9](=[O:22])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:12]=1)(=[O:5])=[O:4])[CH3:2]>[Pd].CO>[CH2:1]([S:3]([CH2:6][CH2:7][N:8]([C@@H:23]([C:25]1[N:26]([C:36]2[CH:37]=[CH:38][C:39]([O:42][CH2:43][C:44]([F:47])([F:45])[F:46])=[CH:40][CH:41]=2)[C:27](=[O:35])[C:28]2[CH2:34][CH2:33][CH2:32][NH:31][C:29]=2[N:30]=1)[CH3:24])[C:9](=[O:22])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([C:18]([F:19])([F:21])[F:20])[CH:12]=1)(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 1

HCID 45101529HCID 45101529, compound

Product 1

HCID 11679210HCID 11679210, compoundYield 104.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of A3 (58 mg, 0.084 mmol) and 10% palladium on carbon (18 mg, 0.017 mmol) in 2 mL of methanol was allowed to stir at room temperature under hydrogen balloon for 20 h. Upon completion, the mixture was filtered through a short column of celite, and the filtrate was concentrated in vacuo and dried to give 61 mg of 1. 1H NMR: a mixture of cis/trans amide rotamers in ca. 3:1 ratio (400 MHz, CDCl3; T=25° C.) δmajor 7.00-7.47 (m, 7H), 5.31 (br s, 1H), 4.71 (q, J=6.62 Hz, 1H), 4.36 (m, 2H), 3.89-4.02 (m, 1H), 3.69-3.76 (m, 1H), 3.36-3.44 (m, 3H), 2.91-3.04 (m, 3H), 2.51-2.66 (m, 2H), 1.87-1.92 (m, 2H), 1.37-1.43 (m, 4H), 1.33 (d, J=6.7 Hz, 3H) and δminor 5.15 (q, J=7.04 Hz, 1H), 4.77 (br s, 1H), 1.28 (d, J=7.08 Hz, 3H). MS (ESI+) 693 [M+H]+.

Workup

  1. filtrationUpon completion, the mixture was filtered through a short column of celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customdried

Sources & evidence

ORD record
ord-2c471c92390b47b7abf2c528e6d68761
Source dataset
uspto-grants-2008_05
Patent number
US07375102B2

Reaction notes

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