Water → HCID 67148882, compound

HRID 910329Notes

Reaction equation

HRID 910329 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].C(N(C(C)C)CC)(C)C.[CH2:23]([O:25][C@@H:26]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([NH:44][CH3:45])[N:39]=2)=[CH:34][CH:33]=1)[C:27]([O:29][CH3:30])=[O:28])[CH3:24].O>ClCCl>[CH2:23]([O:25][C@@H:26]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([N:44]([CH3:45])[C:2]([O:4][C:5]3[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=3)=[O:3])[N:39]=2)=[CH:34][CH:33]=1)[C:27]([O:29][CH3:30])=[O:28])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 67148263HCID 67148263, compound

Product 1

HCID 67148882HCID 67148882, compoundYield 123.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.96 g (4.8 mmol) of 4-nitrophenyl chloroformate and then 0.85 ml (4.8 mmol) of diisopropylethylamine are added to a solution of 1 g (3.2 mmol) of methyl 2(S)-ethoxy-3-[4-(6-methylaminopyrid-2-yl)phenyl]propanoate in 25 ml of dichloromethane. The reaction medium is stirred at room temperature for 1 hour 30 minutes. After addition of water and extraction with dichloromethane, the organic phase is dried over magnesium sulfate, filtered and evaporated. 1.9 g (100%) of methyl 2(S) -ethoxy-3-(4-{6-[methyl-(4-nitrophenoxycarbonyl)amino]pyrid-2-yl}phenyl)propanoate are obtained.

Workup

  1. dry with materialthe organic phase is dried over magnesium sulfate
  2. filtrationfiltered
  3. customevaporated

Sources & evidence

ORD record
ord-d015018115cf434688d6dff4b11c263a
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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