Allyl bromide → HCID 59860576, compound

HRID 37767Notes

Reaction equation

HRID 37767 reaction equation
[C:1]([NH:4][C@H:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:24](Br)[CH:25]=[CH2:26]>CN(C=O)C>[C:1]([NH:4][C@H:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:26][CH:25]=[CH2:24])=[CH:13][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 720751N-Acetyl-D-tyrosine methyl ester

Product 1

HCID 59860576HCID 59860576, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 51 (989 mg, 4.17 mmol), and anhydrous K2CO3 (1.15 g, 8.34 mmol) in DMF (10 mL) was added allyl bromide (1.01 g, 8.34 mmol) and the resulting mixture was allowed to stir for 16 h under a nitrogen atmosphere. The reaction was quenched with water (30 mL), extracted with ethyl acetate (3×30 mL), and the combined organics were washed with water (5×20 mL) before drying. The solvent was evaporated to yield the title compound (985 mg, 3.56 mmol, 85%) as a pale yellow solid. [α]D25-24.2 (c. 0.1, EtOH). Mp 90° C. 1H NMR (CDCl3, 300 MHz): δ 6.97 (d, J=8.7 Hz, 2H, ArH2′ and ArH6′); 6.80 (d, J=8.7 Hz, 2H, ArH3′ and ArH5′); 6.09 (d, J=7.8 Hz, 1H, NH); 6.01 (m, 1H, H2″); 5.37 (dd, J=1.8, 17.4 Hz, 1H, H3a″); 5.25 (dd, J=1.8, 10.5 Hz, 1H, H3b″); 4.80 (m, 1H, H2); 4.47 (d, J=5.5 Hz, 2H, H1″); 3.68 (s, 3H, OCH3); 3.04 (m, 2H, H3); 1.99 (s, 311, NCOCH3). Mass Spectrum (CI, +ve) m/z 278 (100%) [MH+]. HRMS (EI) calcd for C15H19NO4 277.131408, found 277.130309.

Workup

  1. customThe reaction was quenched with water (30 mL)
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washthe combined organics were washed with water (5×20 mL)
  4. custombefore drying
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-00c0c98f0eb2474a936534fe2a54429f
Source dataset
uspto-grants-2013_09
Patent number
US08524657B2

Reaction notes

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