L-Pyroglutamic Acid → HCID 178491775, compound

HRID 2226724Notes

Reaction equation

[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:32]([N:34]([CH2:36][C:37]([NH:39][C@H:40]([C:62]([NH:64][CH2:65][C:66]([OH:68])=[O:67])=[O:63])[CH2:41][CH2:42][CH2:43][NH:44][C:45](=[NH:61])[NH:46][S:47]([C:50]1[C:59]([CH3:60])=[C:57]([CH3:58])[C:54]([O:55][CH3:56])=[CH:53][C:51]=1[CH3:52])(=[O:49])=[O:48])=[O:38])[CH3:35])=[O:33])[CH2:11][S:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].[NH:69]1[C:73](=[O:74])[CH2:72][CH2:71][C@H:70]1[C:75](O)=[O:76]>>[NH:69]1[C:73](=[O:74])[CH2:72][CH2:71][C@H:70]1[C:75]([NH:1][C@H:2]([C:7]([NH:9][C@H:10]([C:32]([N:34]([CH2:36][C:37]([NH:39][C@H:40]([C:62]([NH:64][CH2:65][C:66]([OH:68])=[O:67])=[O:63])[CH2:41][CH2:42][CH2:43][NH:44][C:45](=[NH:61])[NH:46][S:47]([C:50]1[C:59]([CH3:60])=[C:57]([CH3:58])[C:54]([O:55][CH3:56])=[CH:53][C:51]=1[CH3:52])(=[O:49])=[O:48])=[O:38])[CH3:35])=[O:33])[CH2:11][S:12][C:13]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])=[O:76]

Participants

Reactant 2

HCID 7405L-Pyroglutamic Acid

HCID 178491776HCID 178491776, compound

Product 1

HCID 178491775HCID 178491775, compound

Procedure

The coupling and Nα -deprotection processes were repeated in the same manner to prepare H-Asn-Cys(Trt)-Sar-Arg(Mtr)-Gly-resin, followed by another coupling process using pGlu-OH to obtain pGlu-Asn-Cys(Trt)-Sar-Arg(Mtr)-Gly-resin. After drying, the resin was stirred in TFA-anisole-thiophenol (10-1-1 ml) for 4 hours, filtered and washed with TFA.

Sources & evidence

ORD record: ord-5453ff54426f48548dcf254e69e11db9
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05349050

Reaction notes

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