Diisopropylcarbodiimide → Cypate Bombesin

HRID 1879605

反応式

HRID 1879605 の反応式
[CH3:1][C@H:2]([NH:43][C:44]([C@@H:46]([NH:57][C:58]([C@@H:60]([NH:66][C:67]([C@@H:69]([NH:74][C:75]([CH2:77][NH:78][C:79]([C@@H:81]([NH:86][C:87]([C@@H:89]([NH:97][C:98]([C@@H:100]([NH:106][C:107]([C@H:109]1[NH:114][C:112](=[O:113])[CH2:111][CH2:110]1)=[O:108])[CH2:101][CH2:102][C:103]([NH2:105])=[O:104])=[O:99])[CH2:90][CH2:91][CH2:92][NH:93][C:94]([NH2:96])=[NH:95])=[O:88])[CH2:82][CH:83]([CH3:85])[CH3:84])=[O:80])=[O:76])[CH2:70][C:71]([NH2:73])=[O:72])=[O:68])[CH2:61][CH2:62][C:63]([NH2:65])=[O:64])=[O:59])[CH2:47][C:48]1[C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=2[NH:50][CH:49]=1)=[O:45])[C:3]([NH:5][C@H:6]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:24]([NH:26][C@H:27]([C:32]([NH:34][C@H:35]([C:40]([NH2:42])=[O:41])[CH2:36][CH2:37][S:38][CH3:39])=[O:33])[CH2:28][CH:29]([CH3:31])[CH3:30])=[O:25])[CH2:18][C:19]1[NH:23][CH:22]=[N:21][CH:20]=1)=[O:15])=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4].[CH3:115][C:116]1([CH3:161])[C:128](/[CH:129]=[CH:130]/[CH:131]=[CH:132]/[CH:133]=[CH:134]/[CH:135]=[C:136]2\[C:137]([CH3:155])([CH3:154])[C:138]3[C:139]4[CH:140]=[CH:141][CH:142]=[CH:143][C:144]=4[CH:145]=[CH:146][C:147]=3[N:148]\2[CH2:149][CH2:150][C:151]([OH:153])=[O:152])=[N+:127]([CH2:156][CH2:157][C:158]([OH:160])=[O:159])[C:126]2[CH:125]=[CH:124][C:123]3[CH:122]=[CH:121][CH:120]=[CH:119][C:118]=3[C:117]1=2.[Br-:162].C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C>>[CH3:115][C:116]1([CH3:161])[C:128](/[CH:129]=[CH:130]/[CH:131]=[CH:132]/[CH:133]=[CH:134]/[CH:135]=[C:136]2\[C:137]([CH3:154])([CH3:155])[C:138]3[C:139]4[CH:140]=[CH:141][CH:142]=[CH:143][C:144]=4[CH:145]=[CH:146][C:147]=3[N:148]\2[CH2:149][CH2:150][C:151]([OH:153])=[O:152])=[N+:127]([CH2:156][CH2:157][C:158]([OH:160])=[O:159])[C:126]2[CH:125]=[CH:124][C:123]3[CH:122]=[CH:121][CH:120]=[CH:119][C:118]=3[C:117]1=2.[Br-:162].[CH3:1][C@H:2]([NH:43][C:44]([C@@H:46]([NH:57][C:58]([C@@H:60]([NH:66][C:67]([C@@H:69]([NH:74][C:75]([CH2:77][NH:78][C:79]([C@@H:81]([NH:86][C:87]([C@@H:89]([NH:97][C:98]([C@@H:100]([NH:106][C:107]([C@H:109]1[NH:114][C:112](=[O:113])[CH2:111][CH2:110]1)=[O:108])[CH2:101][CH2:102][C:103]([NH2:105])=[O:104])=[O:99])[CH2:90][CH2:91][CH2:92][NH:93][C:94]([NH2:96])=[NH:95])=[O:88])[CH2:82][CH:83]([CH3:84])[CH3:85])=[O:80])=[O:76])[CH2:70][C:71]([NH2:73])=[O:72])=[O:68])[CH2:61][CH2:62][C:63]([NH2:65])=[O:64])=[O:59])[CH2:47][C:48]1[C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=2[NH:50][CH:49]=1)=[O:45])[C:3]([NH:5][C@H:6]([C:10]([NH:12][CH2:13][C:14]([NH:16][C@H:17]([C:24]([NH:26][C@H:27]([C:32]([NH:34][C@H:35]([C:40]([NH2:42])=[O:41])[CH2:36][CH2:37][S:38][CH3:39])=[O:33])[CH2:28][CH:29]([CH3:30])[CH3:31])=[O:25])[CH2:18][C:19]1[NH:23][CH:22]=[N:21][CH:20]=1)=[O:15])=[O:11])[CH:7]([CH3:8])[CH3:9])=[O:4]

参加物

5

反応物 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 10963571CypateHCID 16201612Bombesin

生成物 1

HCID 86612194Cypate Bombesin

実験手順

The resin-bound bombesin analog, i.e. Fmoc-Gln(Trt)-Trp(Boc)-Val-Ala-Gly-His(Trt)-Leu-Met-Lys(Boc)-Rink-Amide resin was assembled from Rink amide-resin (50 mg, 0.031 mmol) based on the conventional Fmoc chemistry. After the N-terminal Fmoc was removed by piperidine in DMF (20%), a solution of Cypate (211.5 mg, 0.3 mmol), HOBT (40.5 mg, 0.30 mmol), DIC (126.0 mg, 0.1 mmol) was added. The resulting mixture was swirled overnight at room temperature. The resin was washed with DMF and DCM, cleaved with a TFA solution (TFA:Phenol:thioanisole:water v:v 85:5:5:5, 4 ml) (2 h), and concentrated. The product was precipitated in cooled tert-butyl methyl ether to afford 2.8 mg of the crude intermediate 16.

後処理

  1. customAfter the N-terminal Fmoc was removed by piperidine in DMF (20%)
  2. washThe resin was washed with DMF and DCM
  3. customcleaved with a TFA solution (TFA:Phenol:thioanisole:water v:v 85:5:5:5, 4 ml) (2 h)
  4. concentrationconcentrated
  5. customThe product was precipitated in cooled tert-butyl methyl ether

出典と根拠

ORDレコード
ord-21060a83fc8c48c89daacddd7a74a649
出典データセット
uspto-grants-2012_11
特許番号
US08318133B2

関連ノート

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