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Citric Acid → Z-Thr(tBu)-Tyr(tBu)-Thr(tBu)-Gln-Asp(OtBu)-Phe-OCH3

HRID 971545
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 971545
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[C@@H:3]([CH3:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[CH3:23]CCCC(F)(F)C(O)CC[C@@H]1[C@@H](CCCCCCC(O)=O)C(=O)C[C@H]1O.C1CCC(NC2CCCCC2)CC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[NH2:76][C@H:77]([C:90]([NH:92][C@H:93]([C:101]([NH:103][C@H:104]([C:110]([NH:112][C@H:113]([C:122]([NH:124][C@H:125]([C:133]([OH:135])=[O:134])[CH2:126][C:127]1[CH:132]=[CH:131][CH:130]=[CH:129][CH:128]=1)=[O:123])[CH2:114][C:115](=[O:121])[O:116][C:117]([CH3:120])([CH3:119])[CH3:118])=[O:111])[CH2:105][CH2:106][C:107](=[O:109])[NH2:108])=[O:102])[C@@H:94]([CH3:100])[O:95][C:96]([CH3:99])([CH3:98])[CH3:97])=[O:91])[CH2:78][C:79]1[CH:84]=[CH:83][C:82]([O:85][C:86]([CH3:89])([CH3:88])[CH3:87])=[CH:81][CH:80]=1>C(OCC)(=O)C.C(#N)C>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([NH:76][C@H:77]([C:90]([NH:92][C@H:93]([C:101]([NH:103][C@H:104]([C:110]([NH:112][C@H:113]([C:122]([NH:124][C@H:125]([C:133]([O:135][CH3:23])=[O:134])[CH2:126][C:127]1[CH:132]=[CH:131][CH:130]=[CH:129][CH:128]=1)=[O:123])[CH2:114][C:115](=[O:121])[O:116][C:117]([CH3:118])([CH3:119])[CH3:120])=[O:111])[CH2:105][CH2:106][C:107](=[O:109])[NH2:108])=[O:102])[C@@H:94]([CH3:100])[O:95][C:96]([CH3:97])([CH3:98])[CH3:99])=[O:91])[CH2:78][C:79]1[CH:80]=[CH:81][C:82]([O:85][C:86]([CH3:87])([CH3:88])[CH3:89])=[CH:83][CH:84]=1)=[O:12])[C@@H:3]([CH3:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 7018812(2S,3R)-2-(((Benzyloxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid2×HCID 7174909515-Hydroxy Lubiprostone Dicyclohexylammonium SaltHCID 131711567H-Tyr(tBu)-Thr(tBu)-Gln-Asp(OtBu)-Phe

Produkt 1

HCID 131711566
Z-Thr(tBu)-Tyr(tBu)-Thr(tBu)-Gln-Asp(OtBu)-Phe-OCH3

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

The acid is liberated from 2.85 g of Z-Thr(tBu)-OH.dicyclohexylammonium salt in ethyl acetate by means of citric acid as described under 23 and the resulting oil consisting of Z-Thr(tBu)-OH is stirred with 3.33 g of H-Tyr(tBu)-Thr(tBu)-Gln-Asp(OtBu)-Phe-OCH 3 in 80 ml of acetonitrile at room temperature. 1.20 g of dicyclohexylcarbodiimde are added thereto in the solid form and the mixture is stirred for 23 hours at room temperature. After filtering off the precipitated dicyclohexylurea, which is washed with three portions of acetonitrile each of 7 ml, the solution is evaporated in vacuo and the residue is three times precipitated from ethyl acetate/alcohol solution by means of petroleum ether.

Aufarbeitung

  1. addition1.20 g of dicyclohexylcarbodiimde are added
  2. filtrationAfter filtering off the precipitated dicyclohexylurea, which
  3. washis washed with three portions of acetonitrile each of 7 ml
  4. customthe solution is evaporated in vacuo
  5. customprecipitated from ethyl acetate/alcohol solution by means of petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-180f94b7c41c4d3ca34899414c115989
Quelldatensatz
uspto-grants-1979_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04159981

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