Hydrochloric Acid → HCID 178501436, compound

HRID 1578294Notes

Reaction equation

[C:1]([NH:11][CH2:12][C:13]([NH:15][C@H:16]([C:23]([NH:25]N)=[O:24])[CH2:17][C:18]1[N:22]=[CH:21][NH:20][CH:19]=1)=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.N([O-])=O.[Na+].C([O-])([O-])=O.[K+].[K+].[C:38]([O:41][CH2:42]C)(=[O:40])[CH3:39]>>[CH3:42][O:41][C:38](=[O:40])[C@H:39]([CH2:4][CH:5]([CH3:10])[CH3:6])[NH:25][C:23](=[O:24])[C@H:16]([CH2:17][C:18]1[N:22]=[CH:21][NH:20][CH:19]=1)[NH:15][C:13](=[O:14])[CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

Reactant 5

HCID 313Hydrochloric Acid

HCID 8857Ethyl Acetate

HCID 11430Potassium Carbonate

HCID 23668193Sodium Nitrite

HCID 178514452HCID 178514452, compound

Product 1

HCID 178501436HCID 178501436, compound

Procedure

21 g of carbobenzoxyglycyl-L-histidine hydrazide is dissolved in 185 ml of 1 N.HCl and to this solution is added 245 ml of ethyl acetate and 4.3 g of NaNO2 at 0° C. with stirring, and after five minutes, 73 ml of a 50% aqueous solution of K2CO3 is added and then this solution is extracted with ethyl acetate. After the extract is dehydrated over anhydrous sodium sulfate, a solution (cooled to 0° C.) of L-leucine methyl ester in ethyl ether (9 g/208 ml) is added to the extract, and this mixture is left to stand overnight at -5° C. The crystals thus produced are filtered off, and washed with ethyl ether to obtain carbobenzoxyglycyl-L-histidyl-L-leucine methyl ester.

Workup

extractionthis solution is extracted with ethyl acetate
additiona solution (cooled to 0° C.) of L-leucine methyl ester in ethyl ether (9 g/208 ml) is added to the extract
waitthis mixture is left
waitto stand overnight at -5° C
customThe crystals thus produced
filtrationare filtered off
washwashed with ethyl ether

Sources & evidence

ORD record: ord-f553492c3f7b42959aa954916fbe0b7e
Source dataset: uspto-grants-1981_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04292404

Reaction notes

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