tert-Butyl bromoacetate → HCID 54257363, compound

HRID 2185585Notes

Reaction equation

HRID 2185585 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:16])[C@H:7]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH2:8])([CH3:4])[CH3:3].Br[CH2:18][CH2:19][O:20]C1CCCCO1.C(N(C(C)C)CC)(C)C.Br[CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]>CC#N.CCCCCC>[CH3:4][C:2]([O:5][C:6](=[O:16])[C@H:7]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[N:8]([CH2:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:18][CH2:19][OH:20])([CH3:1])[CH3:3]

Participants

7

Reactant 4

HCID 79177tert-Butyl bromoacetateHCID 81531Diisopropylethylamine2×HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 6931633tert-butyl (2S)-2-amino-3-phenylpropanoate

Product 1

HCID 54257363HCID 54257363, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8058HexaneSolvent

Procedure

A solution of L-phenylalanine 1,1-dimethylethyl ester (221.3 g; 1 mol), 2-(2-bromoethoxy)-tetra-hydropyran, prepared according to J. Org. Chem. 1986, 51, 752-755 (282.3 9; 1.35 mol) and diisopropylethylamine (commercial product) (175 mL; 1 mol) in CH3CN (1 L) was refluxed for 14 h. Diisopropylethylamine (commercial product) (175 mL; 1 mol) and tert-butyl bromoacetate (commercial product) (233 g; 1.2 mol) were added and the mixture refluxed for further 2 h. The solution was evaporated to give a residue which was dissolved in n-hexane (2 L) and washed with H2O (1,4L), 1 N HCl (500 mL), 1 N NaOH (100 mL) and H2O (200 mL). The solution was evaporated and the residue was dissolved in MeOH (2 L) and 2 N HCl (1 L) was added. After 2 h, 2 N NaOH (1.2 L) was added, the solution was evaporated to remove methanol and n-hexane (2 L) was added to extract the product. The organic solution was evaporated to obtain the desired product (280 g; 0.738 mol). The product was utilised for the following step without further purification.

Workup

  1. temperaturethe mixture refluxed for further 2 h
  2. customThe solution was evaporated
  3. customto give a residue which
  4. washwashed with H2O (1,4L), 1 N HCl (500 mL), 1 N NaOH (100 mL) and H2O (200 mL)
  5. customThe solution was evaporated
  6. dissolutionthe residue was dissolved in MeOH (2 L)
  7. addition2 N HCl (1 L) was added
  8. addition2 N NaOH (1.2 L) was added
  9. customthe solution was evaporated
  10. customto remove methanol and n-hexane (2 L)
  11. additionwas added
  12. extractionto extract the product
  13. customThe organic solution was evaporated

Sources & evidence

ORD record
ord-604ca301f1fb4209ab908ae9dd7b31d8
Source dataset
uspto-grants-2002_06
Patent number
US06403055B1

Reaction notes

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