Reaction #435993

Reaction equation

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

3-(aminosulfonyl)-5-[(dipropylamino)-carbonyl]benzoic acid

(2R,3S)-3-amino-1-[(3-methoxybenzyl)-amino]-4-phenyl-2-butanol

(2R,3S)-3-amino-4-(3,5-difluorophenyl)-1-[(3-methoxybenzyl)amino]-2-butanol Trifluoroacetate

→

title compound

5-(Aminosulfonyl)-N1-{(1S,2R)-1-benzyl-2-hydroxy-3-[(3-methoxybenzyl)amino]propyl}-N3,N-dipropylisophthalamide

Solvents

DMF

Conditions

Workup

1. 1
   Otherpartitioned between ethyl acetate and water
2. 2
   OtherThe organic phase is separated
3. 3
   Washwashed with saline
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated

Procedure

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 0.0928 g, 0.244 mmol) is added to a mixture of, 3-(aminosulfonyl)-5-[(dipropylamino)-carbonyl]benzoic acid (XXXIX, PREPARATION 13, 0.0800 g, 0.244 mmol) and (2R,3S)-3-amino-1-[(3-methoxybenzyl)-amino]-4-phenyl-2-butanol (VIII, EXAMPLE 175, 0.0732 g, 0.244 mmol) in dry DMF (3 mL). The mixture is stirred for 18 hours at 20–25 degrees, and then partitioned between ethyl acetate and water. The organic phase is separated and washed with saline, dried over anhydrous sodium sulfate, filtered and concentrated. The concentrate is column chouromatographed (silica gel; methanol/dichloromethane, 5/95) to give the title compound, MS (ESI+) for C32H42N4O6S m/z (M+H)+=611.5; HRMS (FAB) calculated for C32H42N4O6S+H1=611.2903, found=611.2904.

Source