Hydrochloric Acid → HCID 178501421, compound

HRID 1580873Notes

Reaction equation

HRID 1580873 reaction equation
[NH:1]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[C@H:2]([C:15]([NH:17][C@H:18]([C:26]([NH:28]N)=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].Cl.N(OC(C)(C)C)=O.[CH3:48][O:49][C:50]([C@@H:52](N)[CH2:53][C:54]1[NH:58][CH:57]=[N:56][CH:55]=1)=[O:51].Cl.Cl>CN(C)C=O.O1CCOCC1.O.C(N(CC)CC)C>[NH:1]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[C@H:2]([C:15]([NH:17][C@H:18]([C:26]([NH:28][C@H:52]([C:50]([O:49][CH3:48])=[O:51])[CH2:53][C:54]1[N:58]=[CH:57][NH:56][CH:55]=1)=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 2723645Methyl L-histidinate dihydrochlorideHCID 131709972Z-Lys(BOC)-Phe-NH-NH2

Product 1

HCID 178501421HCID 178501421, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent3×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

5.4 g of Z-Lys(BOC)-Phe-NH-NH2 in 40 ml of dimethylformamide are mixed at -16°C with 6.8 ml of 3.66 N HCl in dioxane and then with 1.5 ml of t-butyl nitrite. After 10 minutes at -10°C to -15°C, 3.5 ml of triethylamine are added. 3.64 g of H-His-OMe. 2 HCl are added in the solid form and 4.2 ml of triethylamine are thereafter added dropwise. The mixture is allowed to warm to 0°C over the course of 1 hour, with a pH of about 7 being set up by adding a total of 0.8 ml of triethylamine. After stirring overnight at 0°C the mixture is poured into 250 ml of water and the smeary product is obtained in the form of a powder by triturating with water. In a thin layer chromatogram on silica gel in chloroform-methanol (9:1) Rf = 0.4. Melting point 136°-137°C (from ethyl acetate).

Workup

  1. additionare thereafter added dropwise
  2. customthe smeary product is obtained in the form of a powder
  3. customby triturating with water

Sources & evidence

ORD record
ord-3aa2ce2b618746859272d581aaa21439
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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