Sodium hydride → HCID 15003986, compound

HRID 1590980

Reaction equation

HRID 1590980 reaction equation
[NH:1]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C@H:2]([C:11]([O:13][CH3:14])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[H-].[Na+].Br[CH2:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30]>CN(C=O)C>[NH:1]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C@H:2]([C:11]([O:13][CH3:14])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:28][C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 62576Benzyl bromoacetateHCID 7010613N-[(Phenylmethoxy)carbonyl]-L-tyrosine methyl ester

Product 1

HCID 15003986HCID 15003986, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under ice-cooling condition, to 25 ml of DMF solution containing 5.70 g of Z-Tyr-OCH3 was added 692 mg of sodium hydride (containing 60%) and the mixture was stirred for 30 minutes, then 3.96 g of benzyl bromoacetate was added thereto and the whole mixture was stirred at 50° C. for 1 hour. The reaction mixture was concentrated under reduced pressure and the residue thus obtained was extracted with 100 ml of ethyl acetate. The ethyl acetate layer was washed with water and a saturated sodium chloride aqueous solution twice, respectively, then dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was added to a silica gel column and eluted with petroleum ether-chloroform (1:4) to obtain 6.00 g (yield: 72.6%) of the above-mentioned objective product.

Workup

  1. temperatureUnder ice-cooling condition
  2. stirringthe whole mixture was stirred at 50° C. for 1 hour
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue thus obtained
  5. extractionwas extracted with 100 ml of ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materiala saturated sodium chloride aqueous solution twice, respectively, then dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue thus obtained
  10. additionwas added to a silica gel column
  11. washeluted with petroleum ether-chloroform (1:4)

Sources & evidence

ORD record
ord-83a3949ee7314cb38bfe64930f149b01
Source dataset
uspto-grants-1993_04
Patent number
US05204326

Linked notes

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