Cesium carbonate → HCID 53746769, compound

HRID 1058853Notes

Reaction equation

HRID 1058853 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].Cl[C:23]1[C:32]2[C:27](=[CH:28][N:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][N:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:9]([O:8][C:6]([NH:5][C@@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:23]2[C:32]3[C:27](=[CH:28][N:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][N:24]=2)=[CH:16][CH:15]=1)[C:3]([O:2][CH3:1])=[O:21])=[O:7])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 7019130Boc-Tyr-OMeHCID 128847741-Chloro-2,6-naphthyridine

Product 1

HCID 53746769HCID 53746769, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To N-(t-butyloxycarbonyl)tyrosine methyl ester (1.42 g, 4.82 mmol) in dry DMF (10 ml) was added 1-chloro-2,6 naphthyridine (0.79 g, 4.82 mmol) and cesium carbonate (1.65 g, 5.06 mmol) and the reaction stirred at 45° under N2 for 2 days. The DMF was evaporated, EtOAc added and washed (3×) with water, dried (MgSO4), and evaporated in vacuo. The residue was chromatographed (SiO2; 40 to 100% EtOAc/isohexane) to afford the title compound as white foam (1.61 g, 82%). δH (CDCl3) 9.29 (1H, s), 8.76 (1H, d, J 5.74 HZ), 8.17 (1H, d, J 5.74 Hz), 8.11 (1H, d, J 5.8 Hz), 7.43 (1H, d, J 5.8 Hz), 7.22-7.18 (3H, m), 5.03 (1H, br s), 4.61 (1H, br s), 3.75 (3H, s), 3.15-3.05 (2H, m), 1.44 (9H, s); m/z (ES+, 70V) MH+424.

Workup

  1. customThe DMF was evaporated
  2. additionEtOAc added
  3. washwashed (3×) with water
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was chromatographed (SiO2; 40 to 100% EtOAc/isohexane)

Sources & evidence

ORD record
ord-a3012dc4a6e54c1bb7a4cc309b069e57
Source dataset
uspto-grants-2003_02
Patent number
US06518283B1

Reaction notes

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