Hydrochloric Acid → HCID 131710008, compound

HRID 971585Notes

Reaction equation

HRID 971585 reaction equation
[NH:1]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][CH2:18][C:19]([O:21]CC)=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].[OH-].[Na+].Cl>CO>[NH:1]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][CH2:18][C:19]([OH:21])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH2:4][S:5][CH3:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131710009HCID 131710009, compound

Product 1

HCID 131710008HCID 131710008, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9.98 g of BOC-Met-Leu-Gly-OEt are dissolved in 300 ml of methanol. 57 ml of 0.59 N sodium hydroxide solution are added over the course of 45 minutes at room temperature and the mixture is stirred for a further hour. Thereafter the pH-value is adjusted to 7 with 0.68 N hydrochloric acid and the solution is evaporated to dryness. The residue is dissolved in ethyl acetate and water and the pH-value is brought to 2 by means of 0.68 N hydrochloric acid. The aqueous phase is extracted by shaking with ethyl acetate. The combined ethyl acetate phases are washed with sodium chloride solution, dried and evaporated. The residue is crystallised from ethyl acetate-hexane. Melting point 137°- 138° C.; [α]D = -31° (c = 2 in dimethylformamide); Rf7 = 0.74 (on silica gel).

Workup

  1. customthe solution is evaporated to dryness
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. extractionThe aqueous phase is extracted
  4. stirringby shaking with ethyl acetate
  5. washThe combined ethyl acetate phases are washed with sodium chloride solution
  6. customdried
  7. customevaporated
  8. customThe residue is crystallised from ethyl acetate-hexane

Sources & evidence

ORD record
ord-61861580bf1f40188e355ef9f0645523
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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