Acetic Acid → HCID 9905205, compound

HRID 1814958Notes

Reaction equation

HRID 1814958 reaction equation
[CH2:1]([O:5]C(Cl)=O)[CH:2](C)C.C(O)(=O)C.C(N(CC)CC)C.[NH2:20][C@H:21]([CH3:39])[CH2:22][CH2:23][CH2:24][CH2:25][N:26]1[C:35](=[O:36])[C:34]2[N:33]([CH3:37])[CH:32]=[N:31][C:30]=2[N:29]([CH3:38])[C:27]1=[O:28]>ClCCl>[C:1]([NH:20][C@H:21]([CH3:39])[CH2:22][CH2:23][CH2:24][CH2:25][N:26]1[C:35](=[O:36])[C:34]2[N:33]([CH3:37])[CH:32]=[N:31][C:30]=2[N:29]([CH3:38])[C:27]1=[O:28])(=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 53803790HCID 53803790, compound

Product 1

HCID 9905205HCID 9905205, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Isobutylchloroformate (341 mg, 2.5 mmol) was added slowly to a solution of acetic acid (146 mg, 2.5 mmol) and triethylamine (252.75 mg, 2.5 mmol) in dichloromethane (20 ml) at −15° C. After warming to room temperature over 15 minutes, a solution of (R)-1-(5-aminohexyl)-3,7-dimethylxanthine (prepared as described for CT11558) (558 mg, 2 mmol) in dichloromethane (10 ml) was added. After stirring al room temperature for 12 hours, the mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 13% methanol-ethyl acetate to provide (R)-1-(5-acetamidohexyl)-3,7-dimethylxanthine (CT12538) (380 mg).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography on silica gel eluting with 13% methanol-ethyl acetate

Sources & evidence

ORD record
ord-724bff77578340e2875e40464c940190
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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