Sodium Hydroxide → Boc-D-Met-Gly-OH

HRID 1277396Notes

Reaction equation

HRID 1277396 reaction equation
[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:2]([C:7]([NH:9][CH2:10][C:11]([O:13]CC)=[O:12])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].[OH-].[Na+]>C(O)C>[NH:1]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@@H:2]([C:7]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])[CH2:3][CH2:4][S:5][CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12919642Ethyl (tert-butoxycarbonyl)-D-methionylglycinate

Product 1

HCID 7019049Boc-D-Met-Gly-OHYield 88.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 20 ml of ethyl alcohol is dissolved 4.7 g of BOC-(D)-Met-Gly-OEt. After cooling, 16 ml of N-aqueous sodium hydroxide solution is added, and the mixture is stirred at room temperature for 1 hour. The ethyl alcohol is distilled off, and the residue, after adding aqueous citric acid solution to neutralize, is extracted with 100 ml of ethyl acetate, followed by washing with water and drying over anhydrous sodium sulphate. The AcOEt isdistilled off and the residue is crystallized with petroleum ether. Recrystallization from AcOEt-petroleum ether results in a yield of 3.8 g of the desired product, m.p. 124°-125° C., Rf1 =0.41, [α]D21 +12.3° (c=0.59, DMF)

Workup

  1. temperatureAfter cooling
  2. distillationThe ethyl alcohol is distilled off
  3. additionthe residue, after adding aqueous citric acid solution
  4. extractionis extracted with 100 ml of ethyl acetate
  5. washby washing with water
  6. dry with materialdrying over anhydrous sodium sulphate
  7. customthe residue is crystallized with petroleum ether
  8. customRecrystallization from AcOEt-petroleum ether

Sources & evidence

ORD record
ord-a77c89b20aa945c790e5a050c1296726
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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