Reaktion #57450

Reaktionsgleichung

DMF

(3S,3aR,6aS) Hexahydrofuro[2,3-b]furan-3-yl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)amino-2-hydroxypropyl)carbamate

2-[(methylsulfonyl)amino]benzimidazol-5-ylsulfonyl chloride

diisopropylethylethyl amine

→

(3S,3aR,6aS)Hexahydrofuro[2,3-b]furan-3-yl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)(2-[(methylsulfonyl)amino]benzimidazol-5-ylsulfonyl)amino-2-hydroxypropyl)carbamate

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to room temperature
2. 2
   SonstigeReaction mixture
3. 3
   Waschenwashed with sat. NaHCO3, 0.5N KHSO4 and brine
4. 4
   TrocknenOrganic phase was dried with MgSO4 and solvent
5. 5
   Sonstigewas removed in vacuo
6. 6
   SonstigePurification by preparative TLC (5% MeOH/EtOAc)
7. 7
   SonstigeRecovered 0.051 g (62%) of the product as a white foam

Vorschrift

(3S,3aR,6aS) Hexahydrofuro[2,3-b]furan-3-yl-N-((1S,2R)-1-benzyl-3-(cyclopentyloxy)amino-2-hydroxypropyl)carbamate (0.050 g, 0.1 mmol) was combined with 2-[(methylsulfonyl)amino]benzimidazol-5-ylsulfonyl chloride (0.055 g, 0.2 mmol) in anhydrous DMF (1 ml) under a N2 atmosphere. The resulting solution was chilled to 0° C. and diisopropylethylethyl amine (0.062 ml, 0.4 mmol) was added. The reaction was allowed to warm to room temperature and stirred for 24 hours. Reaction mixture was diluted in EtOAc and washed with sat. NaHCO3, 0.5N KHSO4 and brine. Organic phase was dried with MgSO4 and solvent was removed in vacuo. Purification by preparative TLC (5% MeOH/EtOAc). Recovered 0.051 g (62%) of the product as a white foam. Rf=0.42 (5% MeOH/EtOAc). 1H NMR (CDCl3) 8.09 (1H,s), 7.76 (1H,d), 7.39 (1H,d), 7.32-7.12 (5H,m), 6.54-6.40 (2H,m), 5.67 (1H,d), 5.10-4.92 (2H,m), 4.85 (1H,m), 4.00-3.83 (3H,m), 3.82-3.70 (2H,m), 3.62-3.51 (1H,m), 3.38 (1H,m), 3.31 (3H,s), 3.10 (1H,m), 3.04-2.80 (4H,m), 1.92-1.70 (6H,m), 1.69-1.44 (4H,m). LRMS (M+H)+ 694.1.

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