Citric Acid → HCID 57120085, compound

HRID 1651022Notes

Reaction equation

HRID 1651022 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:28][CH:29]([CH3:31])[CH3:30])[C@@H:10]([OH:27])[CH:11]=[C:12]([CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[C:13](OCC)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC=CC=1.[H-].C([Al+2])C(C)C.[H-].ClCCl.C(O)(=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:28][CH:29]([CH3:31])[CH3:30])[C@@H:10]([OH:27])[CH:11]=[C:12]([CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[CH2:13][OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 21922555Acetic acid methylene chlorideHCID 57105585HCID 57105585, compoundHCID 86743953HCID 86743953, compound

Product 1

HCID 57120085HCID 57120085, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

16 mg of ethyl (4S,5S)-5-tert-butoxycarbonylamino-4-hydroxy-2-[2-(2-tetrahydropyranyloxy)ethyl]-7-methyl-2-octenoate was dissolved in 0.5 ml of dichloromethane, and 13 μl of boron trifluoride ethyl ether complex was added thereto as -78° C. under stirring. The mixture was stirred for 30 minutes at the same temperature. Then, 75 μl of a 1.5M isobutyl aluminum hydride toluene solution was added to the mixture and further stirred for 45 minutes. 60 μl of a 5M acetic acid dichloromethane solution was added thereto at -78° C., and the reaction solution was raised to room temperature. 10 ml of 10% citric acid aqueous solution was added thereto and extracted with ethyl acetate. The extract was washed sequentially with water and a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 15 mg of (4S,5S)-5-tert-butoxycarbonylamino-1,4-dihydroxy- 2-[2-(2-tetrahydropyranyloxy)ethyl]-7-methyl-2-octene as a colorless oily substance.

Workup

  1. addition13 μl of boron trifluoride ethyl ether complex was added
  2. stirringThe mixture was stirred for 30 minutes at the same temperature
  3. stirringfurther stirred for 45 minutes
  4. temperatureat -78° C., and the reaction solution was raised to room temperature
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed sequentially with water
  7. dry with materiala saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-66d41fda4e1d4ad4b8c259ba2278fe58
Source dataset
uspto-grants-1990_05
Patent number
US04927565

Reaction notes

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