Hydrochloric Acid → HCl-Phe Morpholinamide

HRID 964558Notes

Reaction equation

HRID 964558 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:20]1([C:26]([NH2:28])=[O:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.Cl.C(Cl)(Cl)[Cl:31].CO>O1CCOCC1.C(O)(=O)C>[NH:1]([Cl:31])[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:20]1([C:26]([NH2:28])=[O:27])[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6212ChloroformHCID 131717846Boc-Phe Morpholinamide

Product 1

HCID 131720328HCl-Phe MorpholinamideYield 100%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Boc-Phe-morpholinamide (12.8 g, 38 mmol) was placed in a 250 ml flask, then 4N HCl in dioxane (30 ml) was added. The mixture was stirred for six hours at which time TLC (silica gel; CHCl3 :MeOH:acetic acid, 90:8:2) indicated that the reaction was completed. Dioxane and excess HCl were removed. A white solid, identified by 1HNMR as HCl-Phe-morpholinamide, was obtained in 100 percent yield (10.3 g, 38 mmol).

Workup

  1. customDioxane and excess HCl were removed
  2. customwas obtained in 100 percent yield (10.3 g, 38 mmol)

Sources & evidence

ORD record
ord-2ed59e55cf354c4d8596e5bca3a54dfb
Source dataset
uspto-grants-1998_06
Patent number
US05770573

Reaction notes

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