Water → HCID 86708072, compound

HRID 1524367Notes

Reaction equation

HRID 1524367 reaction equation
[C:1]([O:5][C:6]([N:8]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:10][CH2:11][C:12](OCC)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C[Al]CC(C)C)C.O>C(OCC)C.C1(C)C=CC=CC=1>[C:25]([O:24][C:22]([N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[C@H:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:10][CH2:11][CH:12]=[O:13])=[O:23])([CH3:28])([CH3:26])[CH3:27]

Participants

6

Reactant 3

HCID 962Water2×HCID 16682954DibahHCID 86708071HCID 86708071, compound

Product 1

HCID 86708072HCID 86708072, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of the material from Step 2 (9.73 g, 24.12 mmol) in diethyl ether (240 mL) at −70° C. was slowly added 1.0 M Dibal-H (40.2 mL, 40.2 mmol) in toluene. The reaction mixture was stirred at −70° C. for 45 minutes. Water (10 mL) was slowly added, and the reaction mixture was allowed to warm up to room temperature and aged for 30 minutes. Additional water (80 mL) was added, and aged for 1 hour. It was filtered on a short pad of celite, rinsed with tert-butyl methyl ether (3×). The filtrate was washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford 8.67 g of the title compound that was used without further purification.

Workup

  1. customat −70° C.
  2. temperatureto warm up to room temperature and aged for 30 minutes
  3. waitaged for 1 hour
  4. filtrationIt was filtered on a short pad of celite
  5. washrinsed with tert-butyl methyl ether (3×)
  6. washThe filtrate was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ea36e859747435f806eb68a2f5c6b9d
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

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