Sulfuric Acid → HCID 22178189, compound

HRID 900491Notes

Reaction equation

HRID 900491 reaction equation
[Li+].CC([N-][CH:6]([CH3:8])[CH3:7])C.C([Li])CCC.[CH:14]([NH:17]C(C)C)(C)C.[CH2:21]([O:28][CH2:29][CH2:30][CH:31]=[O:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.S(=O)(=O)(O)O>C1COCC1.CCOCC>[CH2:21]([O:28][CH2:29][CH2:30][CH:31]([OH:32])[C:6]([CH3:7])([CH3:8])[C:14]#[N:17])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 108882613-(Benzyloxy)propanalHCID 178418339Butyllithium

Product 1

HCID 22178189HCID 22178189, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-65 °C

Procedure

5.47 g (79.17 mmol) of isobutyric acid nitrile is added in drops at −65° C. to an LDA solution (produced from 33.64 g (79.17 mmol) of n-butyllithium 15% in hexane, (1.6 M) and 80.1 g (79.17 mmol) of diisopropylamine), and it is stirred for 20 minutes at −65° C. Then, a solution that consists of 10 g (60.9 mmol) of 3-benzyloxy-1-propanaldehyde in 20 ml of THF is added in drops (over 60 minutes). The temperature is kept at −65° C.! Then, it is stirred for one more hour. It is now heated to −20° C., a solution that consists of 20% sulfuric acid is added in drops, and the temperature is allowed to reach +10° C. Then, 50 ml of MTB-ether is added, and then the organic phase is separated. The organic phase is washed with water and then with saturated sodium bicarbonate. Finally, it is washed once more with water and then evaporated to the dry state in a vacuum.

Workup

  1. additionis added in drops (over 60 minutes)
  2. customis kept at −65° C.
  3. stirringThen, it is stirred for one more hour
  4. temperatureIt is now heated to −20° C.
  5. additionis added in drops
  6. customto reach +10° C
  7. customthe organic phase is separated
  8. washThe organic phase is washed with water
  9. washFinally, it is washed once more with water
  10. customevaporated to the dry state in a vacuum

Sources & evidence

ORD record
ord-4152116586a847fb931f43dee2d136ab
Source dataset
uspto-grants-2008_04
Patent number
US07358382B2

Reaction notes

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