Diethyl Ether → HCID 68608925, compound

HRID 1864630Notes

Reaction equation

HRID 1864630 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH2:11][C:12](=[O:16])[C:13]([OH:15])=[O:14])=[CH:4][C:3]=1[CH3:17].C(N(CC)CC)C.[OH-].[Na+].C(OCC)C>C1COCC1>[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([CH2:11][C@@H:12]([OH:16])[C:13]([OH:15])=[O:14])=[CH:4][C:3]=1[CH3:17]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 68610814HCID 68610814, compound

Product 1

HCID 68608925HCID 68608925, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere a solution of 12.0 g (37.4 mmol) (1R)-B-chloro-diisopinocampheyl borane in 40 mL THF was added dropwise to a solution, cooled to −35° C., of 6.5 g (26.0 mmol) 3-(4-amino-3-methyl-5-nitro-phenyl)-2-oxo-propionic acid and 4.5 mL (32.4 mmol) triethylamine in 100 mL THF within 15 min and the reaction solution was stirred overnight at RT. Then the reaction solution was carefully combined at 5° C. with 60 mL of 1 M NaOH and 150 mL diethyl ether and stirred for 15 min. The organic phase was separated off, extracted three times with 40 mL of 1 M NaOH and once with 40 mL water. The combined aqueous phases were acidified with semiconc. HCl while cooling with an ice bath and extracted twice with in each case 120 mL EtOAc. The combined organic phases were dried on Na2SO4 and evaporated down i. vac. The crude product was obtained, which was reacted further without purification.

Workup

  1. stirringstirred for 15 min
  2. customThe organic phase was separated off
  3. extractionextracted three times with 40 mL of 1 M NaOH
  4. temperatureHCl while cooling with an ice bath
  5. extractionextracted twice with in each case 120 mL EtOAc
  6. customThe combined organic phases were dried on Na2SO4
  7. customevaporated down i

Sources & evidence

ORD record
ord-360ae61972d241b6bb8592906ee95ec0
Source dataset
uspto-grants-2009_12
Patent number
US07625886B2

Reaction notes

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