Diethyl Ether → HCID 86756889, compound

HRID 1979200Notes

Reaction equation

HRID 1979200 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:38][CH:39]([CH3:41])[CH3:40])[C:22]([NH:24][N:25]([C:30](=[O:37])[CH:31]([O:33]C(=O)C)[CH3:32])[CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10].C(=O)([O-])[O-].[K+].[K+].C(OCC)C>CO.O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:9]([C@H:11]([C@@H:21]([CH2:38][CH:39]([CH3:41])[CH3:40])[C:22]([NH:24][N:25]([C:30](=[O:37])[CH:31]([OH:33])[CH3:32])[CH2:26][CH:27]([CH3:29])[CH3:28])=[O:23])[CH2:12]/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:10]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 86756890HCID 86756890, compound

Product 1

HCID 86756889HCID 86756889, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 1.11 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-(2(RS)-acetoxypropionyl)-2′-isobutyl-4-methylvalerohydrazide in a mixture of 8 ml of methanol and 4 ml of water was treated with 0.524 g of potassium carbonate. The mixture was stirred at room temperature for 2 hours, diluted with water and extracted with ethyl acetate. The ethyl acetate solution was washed with water, dried over anhydrous magnesium sulphate and was evaporated to give a foam. Trituration of this foam with diethyl ether gave 0.71 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-(2(RS)-hydroxypropionyl)-2′-isobutyl-4-methylvalerohydrazide in the form of a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate solution was washed with water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. customwas evaporated
  5. customto give a foam

Sources & evidence

ORD record
ord-1e1e4fa8286f4c32a880524e8c01bb0a
Source dataset
uspto-grants-2001_05
Patent number
US06239151B1

Reaction notes

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