Pyridine → HCID 69598145, compound

HRID 724588Notes

Reaction equation

HRID 724588 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[S:24][N:23]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:22](=[O:29])[CH:21]=2)=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.[N:45]1C=CC=CC=1.CN(C=O)C>O1CCOCC1.CCOC(C)=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:10](=[O:12])[NH2:45])[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[S:24][N:23]([C:25]([CH3:27])([CH3:28])[CH3:26])[C:22](=[O:29])[CH:21]=2)=[CH:18][CH:19]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 90495Di-tert-butyl dicarbonateHCID 69598121HCID 69598121, compound

Product 1

HCID 69598145HCID 69598145, compoundYield 139.3%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-F (0.76 g, 1.8 mmol), Boc2O (0.52 g, 2.4 mmol), pyridine (99 μL, 1.3 mmol), and NH4CO3H (0.22 g, 2.8 mmol) in dioxane (4 mL) and DMF (1 mL) was stirred at 25° C. for 12 h. The reaction mixture was diluted with EtOAc (100 mL) and washed with 0.1 N HCl (2×20 mL), saturated NaHCO3 (2×20 mL), and brine (20 mL), dried with Na2SO4, filtered, and concentrated to give a crude residue which was purified using flash column chromatography (100% CH2Cl2→10% MeOH/CH2Cl2) to yield 1-G as a brown-red solid (0.76 g, 100%). 1H NMR (400 MHz, CDCl3): δ 7.41 (d, J=8.2 Hz, 2H), 7.30 (d, J=8.2 Hz, 2H), 6.38 (s, 1H), 6.01 (br s, 1H), 5.45 (br s, 1H), 5.15–5.10 (m, 1H), 4.50–4.38 (m, 1H), 3.15 (dd, J=13.9, 6.8 Hz, 1H), 3.08 (dd, J=13.5, 6.5 Hz, 1H), 1.68 (s, 9H), 1.41 (s, 9H); LCMS found for C21H30N3O4S (M+H)+: m/z=420.

Workup

  1. washwashed with 0.1 N HCl (2×20 mL), saturated NaHCO3 (2×20 mL), and brine (20 mL)
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude residue which
  6. customwas purified

Sources & evidence

ORD record
ord-98aacd7b53e845a197feb48e985e1a45
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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