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Dicyclohexylcarbodiimide → N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine, methyl ester

HRID 393053
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 393053
CC(C)(O[C:5]([NH:7][C@H:8]([C:28]([O:30][CH3:31])=[O:29])[CH2:9][NH:10][C:11]([O:13][CH2:14][CH:15]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])=[O:6])C.C1C2C(COC(NC[C@@H](C(OC)=O)N)=O)C3C(=CC=CC=3)C=2C=CC=1.F[C:59](F)(F)[C:60]([OH:62])=O.ClCCl.[Cl:68][C:69]1[CH:77]=[C:76]([C:78]([NH:80][CH2:81][C:82]2[CH:87]=CC=[C:84](O)[CH:83]=2)=[O:79])[CH:75]=[CH:74][C:70]=1C(O)=O.C1C=NC2N(O)N=NC=2C=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.O>[Cl:68][C:69]1[CH:77]=[C:76]([C:78]([NH:80][CH2:81][C:82]2[CH:83]=[CH:84][CH:59]=[C:60]([OH:62])[CH:87]=2)=[O:79])[CH:75]=[CH:74][C:70]=1[C:5]([NH:7][C@H:8]([C:28]([O:30][CH3:31])=[O:29])[CH2:9][NH:10][C:11]([O:13][CH2:14][CH:15]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])=[O:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 6

HCID 10868DicyclohexylcarbodiimideHCID 181649HOAtHCID 21863450Trifluoroacetic acid methylene chlorideHCID 226613972-Chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoic acidHCID 59977282(S)-2-tert-butoxycarbonylamino-3-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid methyl ester
HCID 69512100
3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine, methyl ester

Produkt 1

HCID 131723024N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine, methyl esterAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N-[(1,1-dimethylethoxy)carbonyl]-3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine, methyl ester (Example 62; 1.50 g, 3.4 mmol) was converted to crude 3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine, methyl ester (1.30 g, 112% of the theoretical amount) by treatment with trifluoroacetic acid/dichloromethane (1:1). A portion of this material (0.50 g) was combined with 2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoic acid (449 mg, 1.5 mmol), HOAT (219 mg, 1.6 mmol) and dicyclohexylcarbodiimide (363 mg, 1.8 mmol) in N,N-dimethylformamide (5 mL) and the reaction mixture was stirred at room temperature over the weekend. Water was added and the mixture was extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, dried, filtered, evaporated, and chromatographed (2-10% methanol/dichloromethane) to give N-[2-chloro-4-[[[(3-hydroxyphenyl)methyl]amino]carbonyl]benzoyl]-3-[(9H-fluoren-9-ylmethoxy)carbonyl]amino-L-alanine, methyl ester (0.57 g, 62%) as a white solid.

Aufarbeitung

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with water and brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customchromatographed (2-10% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-0ebe6c892df248b5ac7fc53c286791a3
Quelldatensatz
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06803384B2

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