Dicyclohexylcarbodiimide → HCID 178427520, compound

HRID 467359Notes

Reaction equation

HRID 467359 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:10]([NH:12][C@@H:13]([C:31]([NH:33][C@H:34]([C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[CH:38][CH:37]=1)=[O:32])[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:30])[NH:19][S:20]([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:67]([C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[C@H:68]([C:78]([OH:80])=O)[CH2:69][O:70][CH2:71][C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1.C1C2C3C(=O)N(O)C(=O)C3C1C=C2.C1CCC(N=C=NC2CCCCC2)CC1>>[NH:67]([C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[C@H:68]([C:78]([NH:1][C@H:2]([C:10]([NH:12][C@@H:13]([C:31]([NH:33][C@H:34]([C:50]([O:52][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:51])[CH2:35][C:36]1[CH:37]=[CH:38][C:39]([O:42][CH2:43][C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)=[CH:40][CH:41]=1)=[O:32])[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:30])[NH:19][S:20]([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:21])=[O:22])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:80])[CH2:69][O:70][CH2:71][C:72]1[CH:73]=[CH:74][CH:75]=[CH:76][CH:77]=1

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dioneHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 178427521HCID 178427521, compound

Product 1

HCID 178427520HCID 178427520, compound

Procedure

Using 3.90 g Boc-Phe-D-Arg(Tos)-Tyr(Bzl)-OBzl, 1.60 g Boc-Ser(Bzl)-OH, 1.08 g HONB and 1.24 g DCC, the desired product was obtained in exactly the same manner as in Example 1-(III).

Sources & evidence

ORD record
ord-179f9939a8654510ae0a5e3300089ff6
Source dataset
uspto-grants-1992_10
Patent number
US05159061

Reaction notes

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