Dichloromethane → N-BOC-S-trityl-cysteine 4-amino-2-(3,5-dimethylphenyl)benzoyl methionine methyl ester

HRID 1739145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1739145
[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26])[NH:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[CH:15]=1.C(Cl)Cl.CCN(CC)CC.[C:38]([NH:45][C@H:46]([C:68]([OH:70])=[O:69])[CH2:47][S:48][C:49]([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)([C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].COC(=O)[C@H](CCSC)NC(=O)C1C=CC(N)=CC=1>C1COCC1>[C:38]([NH:45][C@H:46]([C:68]([OH:70])=[O:69])[CH2:47][S:48][C:49]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)([C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].[CH3:1][O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH2:24][S:25][CH3:26])[NH:5][C:6](=[O:22])[C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[C:14]1[CH:15]=[C:16]([CH3:21])[CH:17]=[C:18]([CH3:20])[CH:19]=1

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 186667574-Amino-2-(3,5-dimethylphenyl)benzoyl methionine methyl esterHCID 67565269N-BOC-S-trityl-cysteine 4-aminobenzoyl methionine methyl ester

Produkt 1

HCID 67601032N-BOC-S-trityl-cysteine 4-amino-2-(3,5-dimethylphenyl)benzoyl methionine methyl esterAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-amino-2-(3,5-dimethylphenyl)benzoyl methionine methyl ester (0.10 g, 0.26 mmol) was dissolved into dry CH2Cl2 (1.4 ml) and it was allowed to stand. In another flask, N-BOC-S-trityl-Cys (0.12 g, 0.26 mmol) was dissolved into THF (4.4 ml) and was reacted with IBCF (0.03 ml) and Et3N (0.04 ml) as described above. The product was worked up as described for N-BOC-S-trityl-cysteine-4-aminobenzoyl methionine methyl ester in Example 1 and chromatographed on silica gel using a 1:1 hexanes and ethyl acetate elution mixture to give 0.12 g (56.0%) of pure material. 1H NMR (CDCl3) 1.33 (9H, s), 1.61-1.68 (1H, m), 1.73-1.91 (4H, m), 1.96 (2H, t, J=7.6 Hz), 2.24 (6H, s), 2.57-2.64 (2H, m), 3.57 (3H, s), 4.00 (1H, br s), 4.54-4.58 (1H, m), 5.84 (1H, d, J=7.8 Hz), 5.97 (1H, br d), 6.90 (1H, s) , 6.92 (2H, s) , 7.18-7.22 (9H, m), 7.27-7.40 (7H, m), 7.55 (1H, m), 7.61 (1H, m), 8.58 (1H, br s); 13C NMR (CDCl3) 15.11, 21.20, 27.79, 29.25, 31.28, 51.70, 52.28, 54.08, 60.32, 71.45, 80.75, 118.01, 120.80, 126.38, 126.82, 127.98, 129.41, 129.87, 130.22, 138.11, 139.18, 139.79, 141.06, 144.17, 168.38, 169.04, 171.82.

Aufarbeitung

  1. customchromatographed on silica gel using
  2. washa 1:1 hexanes and ethyl acetate elution mixture

Quellen und Nachweise

ORD-Eintrag
ord-6395b33658a94446b65bbb8b7d524791
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05965539

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