Cesium carbonate → HCID 59873686, compound

HRID 1698927Notes

Reaction equation

HRID 1698927 reaction equation
[C:1]([O:5][C:6](=[O:27])[C@H:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)[NH:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])([CH3:4])([CH3:3])[CH3:2].Br[CH2:29][CH2:30][CH2:31][OH:32].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[OH:32][CH2:31][CH2:30][CH2:29][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][C@H:7]([NH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:27])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 123083-Bromo-1-propanolHCID 11428694Z-Tyr-OtBu

Product 1

HCID 59873686HCID 59873686, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(benzyloxycarbonyl)-L-tyrosine tert-butyl ester (0.37 g, 1.0 mmol), 3-bromo-1-propanol (0.09 mL, 1.0 mmol), and cesium carbonate (0.33 g, 1.0 mmol) in anhydrous N,N-dimethylformamide (5 mL) was stirred at room temperature for 24 h. The reaction mixture was evaporated to dryness under high vacuum and the residue was partitioned between water and ethyl acetate. The aqueous layer was separated and extracted with ethyl acetate. The ethyl acetate extracts were combined and washed once with saturated sodium bicarbonate and brine. The ethyl acetate was dried and evaporated to dryness. The residue was purified on a silica gel column (10 g Waters Sep-Pak) by eluting with a gradient of ethyl acetate and hexane from 20:80 to 30:70. The pure fractions were combined and evaporated to dryness to give the title compound (0.269 g, 63% yield) as a clear oil. 1H NMR (300 MHz, CDCl3) δ7.34 (m, 5H), 7.05 (d, J=8.6 Hz, 2H), 6.80 (m, 2H), 5.22 (d, J=8.1 Hz, 1H), 5.10 (d, J=2.8 Hz, 2H), 4.48 (q, J=8.1 Hz, 1H), 4.09 (t, J=6.0 Hz, 2H), 3.86 (t, J=6.0 Hz, 2H), 3.02 (m, 2H), 2.03 (p, J=6.0 Hz, 2H), 1.41 (s, 9H).

Workup

  1. customThe reaction mixture was evaporated to dryness under high vacuum
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate
  5. washwashed once with saturated sodium bicarbonate and brine
  6. dry with materialThe ethyl acetate was dried
  7. customevaporated to dryness
  8. customThe residue was purified on a silica gel column (10 g Waters Sep-Pak)
  9. washby eluting with a gradient of ethyl acetate and hexane from 20:80 to 30:70
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-34439fed6fe74014a5aedeabe60b09dc
Source dataset
uspto-grants-2002_02
Patent number
US06344484B1

Reaction notes

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