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N-methyl-2-pyrrolidone → n-[(2,2-Dichloro-1-methylcyclopropyl)carbonyl]-4-[[(2,4,6-trimethylphenyl)carbonyl]amino]-l-phenylalanine

HRID 393440
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 393440
CC1C=C(C)C=C(C)C=1S([NH:13][C:14]1[CH:25]=[CH:24][C:17]([CH2:18][C@@H:19]([C:21]([OH:23])=[O:22])[NH2:20])=[CH:16][CH:15]=1)(=O)=O.[Cl:26][C:27]1([Cl:34])[CH2:29][C:28]1([CH3:33])[C:30](O)=[O:31].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:46]2[CH:47]=C[CH:49]=[CH:50][C:45]=2N=N1.[CH3:62]CN(C(C)C)C(C)C.CN1[CH2:76][CH2:75][CH2:74][C:73]1=[O:77]>>[Cl:26][C:27]1([Cl:34])[CH2:29][C:28]1([C:30]([NH:20][C@H:19]([C:21]([OH:23])=[O:22])[CH2:18][C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:73]([C:74]2[C:50]([CH3:49])=[CH:45][C:46]([CH3:47])=[CH:76][C:75]=2[CH3:62])=[O:77])=[CH:25][CH:24]=1)=[O:31])[CH3:33]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 1026212,2-Dichloro-1-methylcyclopropanecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 544513294-[[(2,4,6-trimethylphenyl)sulfonyl]amino]-L-phenylalanine

Produkt 1

HCID 54131599
n-[(2,2-Dichloro-1-methylcyclopropyl)carbonyl]-4-[[(2,4,6-trimethylphenyl)carbonyl]amino]-l-phenylalanine

Versuchsvorschrift

4-[[(2,4,6-Trimethylphenyl)sulfonyl]amino]-L-phenylalanine on Wang resin (0.30 g, 0.23 mmol), 2,2-dichloro-1-methylcyclopropane carboxylic acid (0.19 g, 1.14 mmol), BOP ((0.50 g, 1.14 mmol) and DIPEA (0.26 mL, 1.5 mmol) in N-methylpyrrolidinone (3 mL) was agitated for 3 hr. The mixture was filtered and the resin was washed with dichloromethane and methanol and was air dried. Treatment with 90% TFA in dichloromethane for 3 min effected cleavage from the resin. The mixture was filtered, the filtrate was concentrated and lyophilized from water to give N-[(2,2-dichloro-1-methylcyclopropyl)carbonyl]-4-[[(2,4,6-trimethylphenyl)carbonyl]amino]-L-phenylalanine as a white solid.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washthe resin was washed with dichloromethane and methanol
  3. customdried
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-ad849bd6f0684d38bb4a769cc773c319
Quelldatensatz
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06806365B2

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