Acetic Anhydride → 1,2-dibenzyl 1-tert.butyl 1-(3-acetoxypropyl)-4-methyl-1,1,2(R)-pentanetricarboxylate

HRID 1464365Notes

Reaction equation

HRID 1464365 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C@H:6]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:7][CH:8]([CH3:10])[CH3:9].[C:38](OC(=O)C)(=[O:40])[CH3:39]>N1C=CC=CC=1>[C:38]([O:1][CH2:2][CH2:3][CH2:4][C:5]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C@H:6]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:7][CH:8]([CH3:9])[CH3:10])(=[O:40])[CH3:39]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 678262341,2-dibenzyl 1-tert.butyl 1-(3-hydroxypropyl)-4-methyl-1,1,2(R)-pentanetricarboxylate

Product 1

HCID 678264901,2-dibenzyl 1-tert.butyl 1-(3-acetoxypropyl)-4-methyl-1,1,2(R)-pentanetricarboxylateYield 99.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1.069 g of 1,2-dibenzyl 1-tert.butyl 1-(3-hydroxypropyl)-4-methyl-1,1,2(R)-pentanetricarboxylate in 10 ml of pyridine at 0° was treated with 0.643 g of acetic anhydride. The mixture was stirred at room temperature for 20 hours and evaporated. The residue was dissolved in ethyl acetate and the solution was washed with 1M hydrochloric acid and with saturated aqueous sodium hydroxide and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation and there were obtained 1.155 g of 1,2-dibenzyl 1-tert.butyl 1-(3-acetoxypropyl)-4-methyl-1,1,2(R)-pentanetricarboxylate in the form of an oil.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe solution was washed with 1M hydrochloric acid and with saturated aqueous sodium hydroxide
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-07fd05323ce24966b547602b203d7e23
Source dataset
uspto-grants-1994_04
Patent number
US05304549

Reaction notes

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