L-Ornithine, N2-[(1,1-dimethylethoxy)carbonyl]-N5-[imino[[(4-methylphenyl)sulfonyl]amino]methyl]- → Boc-Arg(Tos)-Thr(Bzl)-Asn-Thr(Bzl)-Gly-Ser(Bzl)-Gly-Thr(Bzl)-Pro-NH2

HRID 1590971Notes

Reaction equation

HRID 1590971 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:35]([NH:37][CH2:38][C:39]([NH:41][C@H:42]([C:52]([NH:54][CH2:55][C:56]([NH:58][C@H:59]([C:70]([N:72]1[CH2:79][CH2:78][CH2:77][C@H:73]1[C:74]([NH2:76])=[O:75])=[O:71])[C@@H:60]([CH3:69])[O:61][CH2:62][C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)=[O:57])=[O:53])[CH2:43][O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:40])=[O:36])[C@@H:25]([CH3:34])[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:22])[CH2:17][C:18](=[O:20])[NH2:19])=[O:14])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH:87]([C:109]([O:111][C:112]([CH3:115])([CH3:114])[CH3:113])=[O:110])[C@H:88]([C:106](O)=[O:107])[CH2:89][CH2:90][CH2:91][NH:92][C:93](=[NH:105])[NH:94][S:95]([C:98]1[CH:104]=[CH:103][C:101]([CH3:102])=[CH:100][CH:99]=1)(=[O:97])=[O:96]>>[NH:87]([C:109]([O:111][C:112]([CH3:114])([CH3:113])[CH3:115])=[O:110])[C@H:88]([C:106]([NH:1][C@H:2]([C:13]([NH:15][C@H:16]([C:21]([NH:23][C@H:24]([C:35]([NH:37][CH2:38][C:39]([NH:41][C@H:42]([C:52]([NH:54][CH2:55][C:56]([NH:58][C@H:59]([C:70]([N:72]1[CH2:79][CH2:78][CH2:77][C@H:73]1[C:74]([NH2:76])=[O:75])=[O:71])[C@@H:60]([CH3:69])[O:61][CH2:62][C:63]1[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=1)=[O:57])=[O:53])[CH2:43][O:44][CH2:45][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)=[O:40])=[O:36])[C@@H:25]([CH3:34])[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:22])[CH2:17][C:18](=[O:20])[NH2:19])=[O:14])[C@@H:3]([CH3:12])[O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:107])[CH2:89][CH2:90][CH2:91][NH:92][C:93](=[NH:105])[NH:94][S:95]([C:98]1[CH:104]=[CH:103][C:101]([CH3:102])=[CH:100][CH:99]=1)(=[O:97])=[O:96]

Participants

3

Reactant 2

HCID 83767L-Ornithine, N2-[(1,1-dimethylethoxy)carbonyl]-N5-[imino[[(4-methylphenyl)sulfonyl]amino]methyl]-HCID 131717867HCID 131717867, compound

Product 1

HCID 178427597Boc-Arg(Tos)-Thr(Bzl)-Asn-Thr(Bzl)-Gly-Ser(Bzl)-Gly-Thr(Bzl)-Pro-NH2Yield 72.2%

Procedure

By using 8.35 g of Boc-Thr(Bzl)-Asn-Thr(Bzl)-Gly-Ser(Bzl)-Gly-Thr(Bzl)-Pro-NH2 and 3.30 g of Boc-Arg(Tos)-OH, and the same procedure as in Reference 15 was repeated to obtain 7.60 g (yield: 70.5%) of the above-mentioned objective product. Melting point: 120°-132° C.

Sources & evidence

ORD record
ord-6d19f28a60d2416ab2b0d13522c53042
Source dataset
uspto-grants-1993_04
Patent number
US05204326

Reaction notes

Loading…