Nadide (JAN/USAN/INN) → Propan-2-yl 4-bromo-3-hydroxybutanoate

HRID 1816192

Reaction equation

HRID 1816192 reaction equation
P(O)(O)([O-])=O.[K+].P(O)([O-])([O-])=O.[K+].[K+].C1C=[N+]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.CCCCCCCCCC.[Br:68][CH2:69][C:70](=[O:78])[CH2:71][C:72]([O:74][CH:75]([CH3:77])[CH3:76])=[O:73]>CC(O)C>[Br:68][CH2:69][CH:70]([OH:78])[CH2:71][C:72]([O:74][CH:75]([CH3:76])[CH3:77])=[O:73]

Participants

6

Reactant 4

HCID 5893Nadide (JAN/USAN/INN)HCID 15600DecaneHCID 11075004Isopropyl 4-bromo-3-oxobutanoateHCID 21889592Monopotassium phosphate dipotassium phosphate

Product 1

HCID 22492795Propan-2-yl 4-bromo-3-hydroxybutanoate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 50 ml of 50 mM monopotassium phosphate-dipotassium phosphate buffer (pH 7.0) containing 5% of 2-propanol were added 0.1 mmol of NAD+ and 6 g of the washed cells described above. To this mixture was added 50 ml of decane containing 70 mg (0.31 mmol) of isopropyl 4-bromo-3-oxobutanoate, and the mixture was stirred at room temperature for a night and day. Celite was then put into the reaction solution, and stirred for a while and filtered off to separate the resultant solution. The aqueous layer was further extracted three times with ethyl acetate, and combined organic layers were concentrated to give 50 mg of isopropyl 4-bromo-3-hydroxybutanoate.

Workup

  1. stirringstirred for a while
  2. filtrationfiltered off
  3. customto separate the resultant solution
  4. extractionThe aqueous layer was further extracted three times with ethyl acetate
  5. concentrationwere concentrated

Sources & evidence

ORD record
ord-dd56711786f74bf99ae0757b88d9cd15
Source dataset
uspto-grants-2005_04
Patent number
US06884607B2

Linked notes

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