4-Methylmorpholine → 9-Methylene-9H-fluorene

HRID 362129

Reaktionsgleichung

Reaktionsgleichung von HRID 362129
[CH:1]1[C:13]2[CH:12]([CH2:14]OC(N[C@H](C(O)=O)CC3C=CC=CC=3C)=O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O>[CH2:14]=[C:12]1[C:13]2[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=2)[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2

Komponenten

5

Edukt 3

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2761469(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(2-methylphenyl)propanoic acid

Produkt 1

HCID 781479-Methylene-9H-fluorene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3.2 g (8.1 mmol) of N-[(9-fluorenyl)methoxycarbonyl]-3-(2-methylphenyl)-L-alanine and 2.17 g (6.75 mmol) of 2-(1 H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate in 22 ml of dimethylformamide was added to the resin from paragraph viii) and subsequently 1.5 ml (13.5 mmol) of N-methylmorpholine were added. The mixture was agitated for 30 minutes andthen the resin was drained and washed five times with 30 ml of dimethylformamide, twice with 30 ml of dichloromethane, twice with 30 ml of ethyl acetate and twice with 30 ml of diethyl ether. After drying therewere obtained 8.95 g of 5-[4-[[N-[N-[N-[(9-fluorenyl)methoxycarbonyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucyl]-N-[3,3,3-trifluoro-1(RS)-(dimethoxymethyl)propyl]amino]methyl]-3,5-dimethoxyphenoxy]-N-(4-methyl-α-(RS)-phenylbenzyl)valeramide-polystyrene conjugate as a pale brown solid (0.31 mmol/g loading estimated by quantitation of dibenzofulvene at 301 nm).

Aufarbeitung

  1. additionwere added
  2. washwashed five times with 30 ml of dimethylformamide
  3. customAfter drying

Quellen und Nachweise

ORD-Eintrag
ord-a608ac36c83c4499809ab2bdbfad9949
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866684

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