Cesium carbonate → HCID 20806458, compound

HRID 1072472Notes

Reaction equation

HRID 1072472 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:22][C:23]1[CH:24]=[N:25][CH:26]=[C:27]([Cl:32])[C:28]=1[CH2:29]CBr.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:29][C:28]2[C:27]([Cl:32])=[CH:26][N:25]=[CH:24][C:23]=2[Cl:22])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 7019130Boc-Tyr-OMeHCID 22386644HCID 22386644, compound

Product 1

HCID 20806458HCID 20806458, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-Boc-L-tyrosine methyl ester (11.95 g, 40.57 mmol), 3,5-dichloro-4-bromethyl pyridine (see International Patent Application No. PCT/GB99/00589; 10.74 g, 44.56 mmol) and caesium carbonate (14.52 g, 44.56 mmol) in DMF (100 ml) was stirred at room temperature overnight. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and aqueous NaHCO3. The organic layer was washed with citric acid (10%×2), aqueous NaHCO3 (×2) and brine, dried (MgSO4) and concentrated in vacuo to give the title compound as a brown solid (18.0 g, 98%). δH (d6 DMSO) 8.72 (2H, s), 7.25 (1H, d, J 8.2 Hz), 7.19 (2H, d, 18.5 Hz), 6.97 (2H, d, 18.5 Hz), 5.20 (2H, s), 4.13 (1H, m), 3.61 (3H, s), 2.95 (1H, dd, J 13.7, 5.0 Hz), 2.82 (1H, m), 1.32 (9H, s) m/z (ESI, 60V) 477 (M++H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate and aqueous NaHCO3
  3. washThe organic layer was washed with citric acid (10%×2), aqueous NaHCO3 (×2) and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b55d341997874763919833d5eec8e808
Source dataset
uspto-grants-2005_06
Patent number
US06911451B1

Reaction notes

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