Hydrochloric Acid → HCID 178465163, compound

HRID 1415338Notes

Reaction equation

HRID 1415338 reaction equation
N[C@H](C(N[C@H](C(N1CCC[C@H]1C(NCC)=O)=O)CCCNC(=N)N)=O)CSC(C)(C)C.Cl.[NH2:33][C@@H:34]([C:39]([NH:41][C@H:42]([C:49]([NH:51][C@H:52]([C:60]([N:62]1[CH2:71][CH2:70][CH2:69][C@H:63]1[C:64]([NH:66][CH2:67][CH3:68])=[O:65])=[O:61])[CH2:53][CH2:54][CH2:55][NH:56][C:57](=[NH:59])[NH2:58])=[O:50])[CH2:43][S:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:40])[CH2:35][CH:36]([CH3:38])[CH3:37].C([O-])(=O)C.[NH:76]([C:102]([O:104][CH2:105][C:106]1[CH:111]=[CH:110][CH:109]=[CH:108][CH:107]=1)=[O:103])[C@H:77]([C:80]([NH:82][C@H:83]([C:99](O)=[O:100])[CH2:84][C:85]1[CH:90]=[CH:89][C:88]([O:91][CH2:92][C:93]2[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=2)=[CH:87][CH:86]=1)=[O:81])[CH2:78][OH:79].C(N1CCOCC1)C.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C=O.C1C=CC2N(O)N=NC=2C=1>[NH:76]([C:102]([O:104][CH2:105][C:106]1[CH:111]=[CH:110][CH:109]=[CH:108][CH:107]=1)=[O:103])[C@H:77]([C:80]([NH:82][C@H:83]([C:99]([NH:33][C@@H:34]([C:39]([NH:41][C@H:42]([C:49]([NH:51][C@H:52]([C:60]([N:62]1[CH2:71][CH2:70][CH2:69][C@H:63]1[C:64]([NH:66][CH2:67][CH3:68])=[O:65])=[O:61])[CH2:53][CH2:54][CH2:55][NH:56][C:57](=[NH:58])[NH2:59])=[O:50])[CH2:43][S:44][C:45]([CH3:47])([CH3:46])[CH3:48])=[O:40])[CH2:35][CH:36]([CH3:37])[CH3:38])=[O:100])[CH2:84][C:85]1[CH:90]=[CH:89][C:88]([O:91][CH2:92][C:93]2[CH:98]=[CH:97][CH:96]=[CH:95][CH:94]=2)=[CH:87][CH:86]=1)=[O:81])[CH2:78][OH:79]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 73909582HCID 73909582, compoundHCID 178465166HCID 178465166, compoundHCID 178476397HCID 178476397, compound

Product 1

HCID 178465163HCID 178465163, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 757711-HydroxybenzotriazoleCatalystHCID 6228DimethylformamideSolvent

Procedure

In analogy to Example 8(b) 3.6 g (6.8 mmols) of H-Cys(But)-Arg-Pro-NH-C2H5 . 2 HCl were reacted with 3 g of Z-D-Leu-OTcp and worked up. The oily residue (6.1 g of contaminated Z-D-Leu-Cys(But)-Arg-Pro-NH--C2H5) was hydrogenated catalytically in analogy to Example 8(b). Yield: 2.5 g (57%). The compound was strongly contaminated and purified over Sephadex LH 20 in analogy to Example 1(a). Yield: 1.734 g (40%) of H-D-Leu-Cys(But)-Arg-Pro-NH-C2H5 -diacetate. The 1.734 g (2.7 mmols) of H-D-Leu-Cys(But)-Arg-Pro-NH-C2H5 -acetate were reacted in analogy to Example 8(b) with 1.33 g of Z-Ser-Tyr(Bzl)-OH, 0.71 ml of N-ethyl morpholine, 3.65 mg of HOBt and 595 mg of DCC in 5 ml of dimethylformamide and worked up. The substance obtained (2.45 g of Z-Ser-Tyr(Bzl)-D-Leu-Cys(But)-Arg-Pro-NH-C2H5) was hydrogenated catalytically in analogy to Example 8(b) and purified over Sephadex LH 20.

Workup

  1. custompurified over Sephadex LH 20 in analogy to Example 1(a)

Sources & evidence

ORD record
ord-cc6834bc20944f83983d5518656fa2ee
Source dataset
uspto-grants-1977_01
Patent number
US04003884

Reaction notes

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