Hydrochloric Acid → 2-Bromopropionylglycine-benzyl ester

HRID 1952688Notes

Reaction equation

HRID 1952688 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Cl)=[O:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:18]([O:25][C:26](=[O:29])[CH2:27][NH2:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[CH2:18]([O:25][C:26](=[O:29])[CH2:27][NH:28][C:3](=[O:4])[CH:2]([Br:1])[CH3:6])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 979802-Bromopropanoyl chlorideHCID 6451311O-benzylglycine toluene-p-sulphonate

Product 1

HCID 113924092-Bromopropionylglycine-benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

60.97 g (355.7 mmol) of α-bromopropionyl chloride is added in drops at 0° C. to 100 g (296.4 mmol) of glycine benzyl ester p-toluenesulfonic acid salt and 89.98 g (889.2 mmol) of triethylamine in 500 ml of methylene chloride. In this case, the temperature is kept between 0° C.-5° C. 1000 ml of 5% aqueous hydrochloric acid is added, and the organic phase is separated. The organic phase is extracted once more with 500 ml of 5% aqueous hydrochloric acid, dried on magnesium sulfate and evaporated to the dry state in a vacuum. The residue is recrystallized from diisopropyl ether.

Workup

  1. customis kept between 0° C.-5° C
  2. customthe organic phase is separated
  3. extractionThe organic phase is extracted once more with 500 ml of 5% aqueous hydrochloric acid
  4. customdried on magnesium sulfate
  5. customevaporated to the dry state in a vacuum
  6. customThe residue is recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-136a9a20747342a98e7fbc6b96670631
Source dataset
uspto-grants-2000_09
Patent number
US06113880

Reaction notes

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