Water → HCID 86599808, compound

HRID 229851Notes

Reaction equation

HRID 229851 reaction equation
[CH3:1][CH2:2][C@@H:3]([C:5]([O:7][C@@H:8]1[C@@H:13]2[C@@H:14]([CH2:19][CH2:20][C@@H:21]([OH:29])[CH2:22][C@@H:23]([OH:28])[CH2:24][C:25]([O-:27])=[O:26])[C@@H:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[CH:11][C@@H:10]([OH:30])[CH2:9]1)=[O:6])[CH3:4].[Na+].[Br:32][CH2:33][CH2:34][CH2:35][CH2:36]Br.O.C(OCC)C>CN(C)C=O>[Br:32][CH2:33][CH2:34][CH2:35][CH2:36][O:26][C:25](=[O:27])[CH2:24][CH:23]([OH:28])[CH2:22][CH:21]([OH:29])[CH2:20][CH2:19][CH:14]1[CH:13]2[C:12](=[CH:11][CH:10]([OH:30])[CH2:9][CH:8]2[O:7][C:5](=[O:6])[CH:3]([CH3:4])[CH2:2][CH3:1])[CH:17]=[CH:16][CH:15]1[CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 80561,4-DibromobutaneHCID 16759173Pravastatin sodium

Product 1

HCID 86599808HCID 86599808, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of pravastatin sodium (9.25 g, 21 mmol) in N,N-dimethylformamide (70 ml) a mixture of 1,4-dibromobutane (3.68 ml, 31 mmol) in N,N-dimethylformamide (30 ml) was added dropwise. The reaction mixture was stirred at room temperature for 24 h. The solution was then treated with water and diethyl ether, the organic layers were dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography, with n-hexane/ethyl acetate 3/7 as eluent. The title compound was obtained as a white powder (7.8 g).

Workup

  1. additionwas added dropwise
  2. dry with materialthe organic layers were dried with sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography, with n-hexane/ethyl acetate 3/7 as eluent

Sources & evidence

ORD record
ord-0237e2fc24154a10b3a5b89d92950038
Source dataset
uspto-grants-2009_07
Patent number
US07563909B2

Reaction notes

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