Diethyl Ether → HCID 131712167, compound

HRID 894352Notes

Reaction equation

HRID 894352 reaction equation
C([N:11]1[CH2:29][CH2:28][CH2:27][C@H:12]1[C:13]([NH:15][C:16]([C:24]([OH:26])=[O:25])=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14])(OCC1C=CC=CC=1)=O.CCOCC.[BrH:35].CC(O)=O>>[BrH:35].[NH:11]1[CH2:29][CH2:28][CH2:27][C@H:12]1[C:13]([NH:15][C:16]([C:24]([OH:26])=[O:25])=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:14]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 131712165HCID 131712165, compound

Product 1

HCID 131712167HCID 131712167, compoundYield 74%

Procedure

A solution of 0.5 g (0.00125 mole) of N-carbobenzoxy-L-prolyl-dehydrophenylalanine in 3 ml of 32% HBr/HOAc was treated as N-carbobenzoxy-L-prolyl-dehydrophenylalanine azlactone was treated in Example 7(a) except that the ether precipitated product was allowed to stand two days at room temperature before filtration and crystallization from methanol/ethyl acetate to yield 0.313 g (74%) of L-prolyl-dehydrophenylalanine hydrobromide, m.p. 227°-228.5° (dec.), RfA 0.45.

Workup

  1. filtrationto stand two days at room temperature before filtration and crystallization from methanol/ethyl acetate

Sources & evidence

ORD record
ord-4d30b2d8d0974aa097aee4ee2c2c5e73
Source dataset
uspto-grants-1981_08
Patent number
US04283328

Reaction notes

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