4-Methylmorpholine → Z-Pro-Ser(Bzl)-Pro-Arg(NO2)-Gly-NH2

HRID 2226735Notes

Reaction equation

HRID 2226735 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:12]([N:14]1[CH2:39][CH2:38][CH2:37][C@H:15]1[C:16]([NH:18][C@H:19]([C:30]([NH:32][CH2:33][C:34]([NH2:36])=[O:35])=[O:31])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:29])[NH:25][N+:26]([O-:28])=[O:27])=[O:17])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CN1CCOCC1.[N:54]1([C:69]([O:71][CH2:72][C:73]2[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=2)=[O:70])[CH2:68][CH2:67][CH2:66][C@H:55]1[C:56](ON1C(=O)CCC1=O)=[O:57]>Cl.CCOC(C)=O>[N:54]1([C:69]([O:71][CH2:72][C:73]2[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=2)=[O:70])[CH2:68][CH2:67][CH2:66][C@H:55]1[C:56]([NH:1][C@H:2]([C:12]([N:14]1[CH2:39][CH2:38][CH2:37][C@H:15]1[C:16]([NH:18][C@H:19]([C:30]([NH:32][CH2:33][C:34]([NH2:36])=[O:35])=[O:31])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:29])[NH:25][N+:26]([O-:28])=[O:27])=[O:17])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:57]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 8534821,2-Pyrrolidinedicarboxylic acid, 2-(2,5-dioxo-1-pyrrolidinyl) 1-(phenylmethyl) ester, (2S)-HCID 178454225HCID 178454225, compound

Product 1

HCID 178512172Z-Pro-Ser(Bzl)-Pro-Arg(NO2)-Gly-NH2

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

The desired compound was prepared from 1.0 g of Boc-Ser(Bzl)-Pro-Arg(NO2)-Gly-NH2, 10 ml of 4 N HCl-AcOEt, 0.34 ml of NMM and 0.54 g of Z-Pro-OSu in the same manner as in Example 26-(4).

Sources & evidence

ORD record
ord-5de6e2ec4ddb44a783a323dacd0e20a7
Source dataset
uspto-grants-1994_09
Patent number
US05349050

Reaction notes

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