Butyric Acid → HCID 136110737, compound

HRID 458283Notes

Reaction equation

HRID 458283 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[C:16](O)(=[O:20])[CH2:17][CH2:18][CH3:19].[C:22]([O:26][C:27]([NH:29][C@H:30]([C:34]([O:36][CH2:37][CH2:38][C@@H:39]([CH2:52][OH:53])[CH2:40][N:41]1[CH:49]=[N:48][C:47]2[C:46](=[O:50])[NH:45][C:44]([NH2:51])=[N:43][C:42]1=2)=[O:35])[CH:31]([CH3:33])[CH3:32])=[O:28])([CH3:25])([CH3:24])[CH3:23]>ClCCl>[C:22]([O:26][C:27]([NH:29][C@H:30]([C:34]([O:36][CH2:37][CH2:38][C@@H:39]([CH2:52][O:53][C:16](=[O:20])[CH2:17][CH2:18][CH3:19])[CH2:40][N:41]1[CH:49]=[N:48][C:47]2[C:46](=[O:50])[NH:45][C:44]([NH2:51])=[N:43][C:42]1=2)=[O:35])[CH:31]([CH3:33])[CH3:32])=[O:28])([CH3:23])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 264Butyric AcidHCID 10868DicyclohexylcarbodiimideHCID 136201790(R)-9-[4-(N-tert-Butoxycarbonyl-L-valyloxy)-2-hydroxymethylbutyl]guanine

Product 1

HCID 136110737HCID 136110737, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DCC (110 mg, 0.53 mmol) was dissolved in dichloromethane (10 ml) and butyric acid (82 mg, 0.93 mmol) was added. After 4 hours at room temperature the mixture was filtered and the filtrate was evaporated. The residue was dissolved in pyridine (5 ml) and (R)-9-[4-(N-tert-Butoxycarbonyl-L-valyloxy)-2-hydroxymethylbutyl]guanine (200 mg, 0.44 mmol) (Example 1, step a) was added. The mixture was stirred for 120 hours at room temperature. According to TLC the reaction was incomplete and more anhydride was made using the procedure above. This anhydride was added and the mixture was stirred for an additional 20 hours. The reaction mixture was evaporated and chromatographed first on silica gel and then on aluminium oxide, in both cases eluted with dichloromethane/methanol to give 79 mg of the intermediate product.

Workup

  1. filtrationAfter 4 hours at room temperature the mixture was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in pyridine (5 ml)
  4. stirringthe mixture was stirred for an additional 20 hours
  5. customThe reaction mixture was evaporated
  6. customchromatographed first on silica gel
  7. washon aluminium oxide, in both cases eluted with dichloromethane/methanol

Sources & evidence

ORD record
ord-0369146dcd964448931ce0d607da4298
Source dataset
uspto-grants-2007_03
Patent number
US07189849B2

Reaction notes

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