반응 #77839

반응 방정식

BOP

Hunig's base

1-tert-butoxycarbonyl-3-amino-4-(benzyloxycarbonyl)amino-piperidine

4-(aminosulfonyl)benzoic acid

→

tert-butyl (cis)-3-{[4-(aminosulfonyl)benzoyl]amino}-4-{[(benzyloxy)carbonyl]amino}-1-piperidinecarboxylate

수율 45.9%

용매

DMF

반응 조건

후처리

1. 1
   기타then quenched with aqueous NH4Cl
2. 2
   기타The mixture was partitioned between EtOAc and water
3. 3
   세척The organic layer was washed with NaHCO3, 5% LiCl (3×), and brine
4. 4
   기타The organic layer was dried
5. 5
   여과filtered
6. 6
   농축concentrated

실험 절차

1-tert-butoxycarbonyl-3-amino-4-(benzyloxycarbonyl)amino-piperidine (151b) (300 mg) was dissolved in DMF (5 mL) prior to addition of Hunig's base (0.45 mL). 4-(aminosulfonyl)benzoic acid (210 mg) was added followed by BOP (420 mg). The solution was stirred for 8 h then quenched with aqueous NH4Cl. The mixture was partitioned between EtOAc and water. The organic layer was washed with NaHCO3, 5% LiCl (3×), and brine. The organic layer was dried, filtered, and concentrated. Flash chromatography of the residue provided tert-butyl (cis)-3-{[4-(aminosulfonyl)benzoyl]amino}-4-{[(benzyloxy)carbonyl]amino}-1-piperidinecarboxylate (210 mg). MS found: (M−H)−=531.3.

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