HCID 131710181, compound → HCID 131710182, compound

HRID 1606840Notes

Reaction equation

[NH2:1][C@H:2]([C:7]([NH:9][CH2:10][C:11]([NH:13][C@H:14]([C:16]([NH:18][C@H:19]([C:29]([NH:31][C@H:32]([C:41]([NH:43][C@H:44]([C:54]([NH:56][C@H:57]([C:60]([NH:62][C@H:63]([C:65]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])=[O:66])[CH3:64])=[O:61])[CH2:58][OH:59])=[O:55])[CH2:45][CH2:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:42])[CH2:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:30])[CH2:20][CH2:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:17])[CH3:15])=[O:12])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5].[NH:72]([C:193]([O:195][CH2:196][C:197]1[CH:202]=[CH:201][CH:200]=[CH:199][CH:198]=1)=[O:194])[C@H:73]([C:86]([NH:88][C@H:89]([C:102]([NH:104][C@H:105]([C:116]([NH:118][C@H:119]([C:130]([N:132]1[CH2:192][CH2:191][CH2:190][C@H:133]1[C:134]([NH:136][C@H:137]([C:141]([NH:143][C@H:144]([C:157]([NH:159][C@H:160]([C:164]([NH:166][C@H:167]([C:180]([N:182]1[CH2:189][CH2:188][CH2:187][C@H:183]1[C:184](O)=[O:185])=[O:181])[CH2:168][C:169]1[CH:174]=[CH:173][C:172]([O:175][C:176]([CH3:179])([CH3:178])[CH3:177])=[CH:171][CH:170]=1)=[O:165])[CH:161]([CH3:163])[CH3:162])=[O:158])[CH2:145][CH2:146][CH2:147][CH2:148][NH:149][C:150]([O:152][C:153]([CH3:156])([CH3:155])[CH3:154])=[O:151])=[O:142])[CH:138]([CH3:140])[CH3:139])=[O:135])=[O:131])[CH2:120][CH2:121][CH2:122][NH:123][C:124](=[NH:129])[NH:125][N+:126]([O-:128])=[O:127])=[O:117])[CH2:106][CH2:107][CH2:108][NH:109][C:110](=[NH:115])[NH:111][N+:112]([O-:114])=[O:113])=[O:103])[CH2:90][CH2:91][CH2:92][CH2:93][NH:94][C:95]([O:97][C:98]([CH3:101])([CH3:100])[CH3:99])=[O:96])=[O:87])[CH2:74][CH2:75][CH2:76][CH2:77][NH:78][C:79]([O:81][C:82]([CH3:85])([CH3:84])[CH3:83])=[O:80]>CN(C=O)C>[NH:72]([C:193]([O:195][CH2:196][C:197]1[CH:198]=[CH:199][CH:200]=[CH:201][CH:202]=1)=[O:194])[C@H:73]([C:86]([NH:88][C@H:89]([C:102]([NH:104][C@H:105]([C:116]([NH:118][C@H:119]([C:130]([N:132]1[CH2:192][CH2:191][CH2:190][C@H:133]1[C:134]([NH:136][C@H:137]([C:141]([NH:143][C@H:144]([C:157]([NH:159][C@H:160]([C:164]([NH:166][C@H:167]([C:180]([N:182]1[CH2:189][CH2:188][CH2:187][C@H:183]1[C:184]([NH:1][C@H:2]([C:7]([NH:9][CH2:10][C:11]([NH:13][C@H:14]([C:16]([NH:18][C@H:19]([C:29]([NH:31][C@H:32]([C:41]([NH:43][C@H:44]([C:54]([NH:56][C@H:57]([C:60]([NH:62][C@H:63]([C:65]([O:67][C:68]([CH3:69])([CH3:70])[CH3:71])=[O:66])[CH3:64])=[O:61])[CH2:58][OH:59])=[O:55])[CH2:45][CH2:46][C:47](=[O:53])[O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:42])[CH2:33][C:34](=[O:40])[O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:30])[CH2:20][CH2:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:17])[CH3:15])=[O:12])=[O:8])[CH2:3][C:4](=[O:6])[NH2:5])=[O:185])=[O:181])[CH2:168][C:169]1[CH:174]=[CH:173][C:172]([O:175][C:176]([CH3:178])([CH3:179])[CH3:177])=[CH:171][CH:170]=1)=[O:165])[CH:161]([CH3:162])[CH3:163])=[O:158])[CH2:145][CH2:146][CH2:147][CH2:148][NH:149][C:150]([O:152][C:153]([CH3:154])([CH3:156])[CH3:155])=[O:151])=[O:142])[CH:138]([CH3:140])[CH3:139])=[O:135])=[O:131])[CH2:120][CH2:121][CH2:122][NH:123][C:124](=[NH:129])[NH:125][N+:126]([O-:128])=[O:127])=[O:117])[CH2:106][CH2:107][CH2:108][NH:109][C:110](=[NH:115])[NH:111][N+:112]([O-:114])=[O:113])=[O:103])[CH2:90][CH2:91][CH2:92][CH2:93][NH:94][C:95]([O:97][C:98]([CH3:99])([CH3:100])[CH3:101])=[O:96])=[O:87])[CH2:74][CH2:75][CH2:76][CH2:77][NH:78][C:79]([O:81][C:82]([CH3:85])([CH3:83])[CH3:84])=[O:80]

Participants

Conditions

Temperature: 0 °C

Procedure

3.0 g. (2.95 mmoles) of H-25-32-OtBu and 5.46 g. (2.95 mmoles) of Z-Lys(BOC)-Lys(BOC)-Arg(NO2)-Arg(NO2)-Pro-Val-Lys(BOC)-Val-Tyr(tBu)-Pro-OH (Brit. Pat. No. 1 201 053) are dissolved in 33 ml. of DMF. The solution is cooled to 0°C, and 3.35 g. (4.42 mmoles) of DCC-PFPOH complex are added to it. The reaction mixture is kept at 0°C for 15 minutes, thereafter at room temperature for 6 hours. The separated DCU is filtered off, and the filtrate is passed into 450 ml. of dry ether. The separated crude product is filtered off and purified by precipitation from methanol with ether. 7.18 g. (85.1 %) of Z-15-32-OtBu are obtained. Rf3 = 0.35; [α]D = -26.4° (c = 0.42, in DMF).

Workup

dissolution1 201 053) are dissolved in 33 ml
addition(4.42 mmoles) of DCC-PFPOH complex are added to it
waitat room temperature for 6 hours
filtrationThe separated DCU is filtered off
customThe separated crude product
filtrationis filtered off
custompurified by precipitation from methanol with ether

Sources & evidence

ORD record: ord-79ce4308e3e8415ab389eddfd0c0de1e
Source dataset: uspto-grants-1976_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03953415

Reaction notes

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