Hydrochloric Acid → HCID 131711569, compound

HRID 971555Notes

Reaction equation

HRID 971555 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].[ClH:30]>C(OCC)(=O)C>[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].[ClH:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131711561HCID 131711561, compound

Product 1

HCID 131711569HCID 131711569, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3.24 g of BOC-Met-Leu-Gly-OMe are dissolved in 13 ml of 3.8 N hydrogen chloride in ethyl acetate and allowed to stand for 30 minutes at 20° C. On adding 100 ml of petroleum ether the tripeptide ester hydrochloride is precipitated as a sticky mass, and the supernatant solution is decanted off. On triturating with 100 ml of peroxide-free ether at 0° C. a finely powdered product is obtained which is filtered off and dried to constant weight over potassium hydroxide at room temperature in a desiccator. The compound is chromatographically pure but amorphous and strongly hygroscopic. It shows the following Rf-values on silica gel: Rf 43 C = 0.48; Rf (toluene-acetone 1:1) = 0.35.

Workup

  1. customis precipitated as a sticky mass
  2. customthe supernatant solution is decanted off
  3. customOn triturating with 100 ml of peroxide-free ether at 0° C. a finely powdered product
  4. customis obtained which
  5. filtrationis filtered off
  6. dry with materialdried to constant weight over potassium hydroxide at room temperature in a desiccator

Sources & evidence

ORD record
ord-a41656c56a724626884d8a932233bf7b
Source dataset
uspto-grants-1979_07
Patent number
US04159981

Reaction notes

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