Water → HCID 86759275, compound

HRID 431067Notes

Reaction equation

HRID 431067 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[N:10]=[CH:9][C:8]([OH:11])=[C:7]([O:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:6]=1)[CH3:4].[C:18]([O-:21])([OH:20])=O.[Na+].[C:23](Cl)(=[O:31])[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>C(Cl)Cl>[CH:13]1([O:12][C:7]2[C:8]([O:11][C:18]([O:21][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:20])=[CH:9][N:10]=[C:5]([CH:3]([CH3:4])[CH2:2][NH:1][C:23](=[O:31])[O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:6]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 15891Phenyl chloroformateHCID 516892Sodium BicarbonateHCID 18763375HCID 18763375, compound

Product 1

HCID 86759275HCID 86759275, compoundYield 103.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

A mixture of (±)-6-(2-amino-1-methylethyl)4-(cyclopentyloxy)-3-pyridinol (0.037 mol) and NaHCO3 (0.0814 mol) in CH2Cl2 (200 ml) was stirred at 0-5° C. A solution of phenyl carbonochloridate (0.074 mol) in CH2Cl2(50 ml) was added dropwise and the resulting reaction mixture was stirred for one hour at RT. The reaction mixture was poured out into water and the layers were separated. The aqueous phase was extracted twice with CH2Cl2. The combined organic layers were dried, filtered and the solvent evaporated, yielding 18.2 g (±)-phenyl [2-[4-(cyclopentyloxy)-5-[(phenoxycarbonyl) oxy]-2-pyridinyl]propyl]carbamate (interm. 1).

Workup

  1. customthe resulting reaction mixture
  2. stirringwas stirred for one hour at RT
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted twice with CH2Cl2
  5. customThe combined organic layers were dried
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-e783b722a5f64e3facd80583aba0b96f
Source dataset
uspto-grants-2003_12
Patent number
US06656959B1

Reaction notes

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