HCID 178465155, compound → HCID 178468101, compound

HRID 2398512Notes

Reaction equation

HRID 2398512 reaction equation
[NH2:1][C@H:2]([C:8]([NH:10][C@H:11]([C:18]([NH:20][C@H:21]([C:32]([NH:34]N)=[O:33])[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:19])[CH2:12][C:13]1[N:17]=[CH:16][NH:15][CH:14]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[OH:6].N[C@H:37]([C:40]([NH:42][C@H:43]([C:52]([NH:54][C@@H:55]([C:65]([NH:67][C@H:68]([C:73]([NH:75][C@H:76]([C:84]([N:86]1[CH2:95][CH2:94][CH2:93][C@H:87]1[C:88]([NH:90][CH2:91][CH3:92])=[O:89])=[O:85])[CH2:77][CH2:78][CH2:79][NH:80][C:81](=[NH:83])[NH2:82])=[O:74])[CH2:69][CH:70]([CH3:72])[CH3:71])=[O:66])[CH2:56][CH2:57][C:58](=[O:64])[O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:53])[CH2:44][C:45]1[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][CH:46]=1)=[O:41])[CH2:38][OH:39]>>[NH2:1][C@H:2]([C:8]([NH:10][C@H:11]([C:18]([NH:20][C@H:21]([C:32]([NH:34][C@H:37]([C:40]([NH:42][C@H:43]([C:52]([NH:54][C@@H:55]([C:65]([NH:67][C@H:68]([C:73]([NH:75][C@H:76]([C:84]([N:86]1[CH2:95][CH2:94][CH2:93][C@H:87]1[C:88]([NH:90][CH2:91][CH3:92])=[O:89])=[O:85])[CH2:77][CH2:78][CH2:79][NH:80][C:81](=[NH:82])[NH2:83])=[O:74])[CH2:69][CH:70]([CH3:72])[CH3:71])=[O:66])[CH2:56][CH2:57][C:58](=[O:64])[O:59][C:60]([CH3:63])([CH3:61])[CH3:62])=[O:53])[CH2:44][C:45]1[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][CH:46]=1)=[O:41])[CH2:38][OH:39])=[O:33])[CH2:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[NH:25][CH:24]=1)=[O:19])[CH2:12][C:13]1[N:17]=[CH:16][NH:15][CH:14]=1)=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[OH:6].[CH3:2][C:3]([CH2:4][C:5]([OH:6])=[O:7])=[O:39]

Participants

3

Reactant 2

HCID 178465155HCID 178465155, compoundHCID 178514448HCID 178514448, compound

Product 1

HCID 178468101HCID 178468101, compoundYield 30%

Procedure

In analogy to Example 1 f), 500 mg of Glu-His-Trp-NH-NH2 were reacted with 920 mg (1 mmole) of H-Ser-Tyr-D-Glu(OBut)-Leu-Arg-Pro-NH-C2H5 . 2 HCl and purified chromatographically. Yield: 491.5 mg of chromatographically pure material. The content of peptide base was 79% as per UV-spectrum (yield: 30%). [-α]D22 = -31.3° (c=1, dimethyl acetamide)

Workup

  1. custom2 HCl and purified chromatographically
  2. custom[-α]D22 = -31.3° (c=1, dimethyl acetamide)

Sources & evidence

ORD record
ord-6593d55eb84c4ac788e95ee7cf9a52f6
Source dataset
uspto-grants-1977_05
Patent number
US04024248

Reaction notes

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