Biotin → HCID 131724518, compound

HRID 1835740Notes

Reaction equation

HRID 1835740 reaction equation
O[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:3].[C:17]([O:20][C@H:21]([CH3:45])[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]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][NH2:44])[C:27]1=[O:28])(=[O:19])[CH3:18]>CN(C)C=O>[C:17]([O:20][CH:21]([CH3:45])[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]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][NH:44][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:8]2[C@@H:16]3[C@@H:11]([NH:12][C:13]([NH:15]3)=[O:14])[CH2:10][S:9]2)[C:27]1=[O:28])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 171548BiotinHCID 54108424HCID 54108424, compound

Product 1

HCID 131724518HCID 131724518, compoundYield 34.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Disopropylcarbodiimide (113.5 mg, 0.55 mmol) was added to a solution of biotin (122 mg, 0.5 mmol), (R)-1-(5-acetoxyhexyl)-3-(6-aminohexyl)-7-methylxanthine (227 mg, 0.5 mmol) and 4-N,N-dimethylaminopyridine (73.3 mg, 0.6 mmol) in dimethylformamide. After stirring at room temperature for 6 hours, dimethylformamide was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 20% methanol/ethyl acetate to provide (R)-1-(5-acetoxyhexyl)-3-(N-biotinyl-6-aminohexyl)-7-methylxanthine (110 mg).

Workup

  1. customdimethylformamide was evaporated under reduced pressure
  2. customThe residue was purified by flash chromatography on silica gel eluting with 20% methanol/ethyl acetate

Sources & evidence

ORD record
ord-ccb8ceddba0e4bbda6990aabf317ad9a
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

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