Ammonia → HCID 9894791, compound

HRID 1814954Notes

Reaction equation

HRID 1814954 reaction equation
C([O:4][CH:5]([CH3:44])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[CH:16]=[N:15][C:14]=2[N:13]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:43])[CH2:30][CH2:31][CH2:32][CH2:33][C@@H:34]2[C@@H:42]3[C@@H:37]([NH:38][C:39]([NH:41]3)=[O:40])[CH2:36][S:35]2)[C:11]1=[O:12])(=O)C.N>CO.Cl>[C:29]([NH:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][N:13]1[C:14]2[N:15]=[CH:16][N:17]([CH3:21])[C:18]=2[C:19](=[O:20])[N:10]([CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]([OH:4])[CH3:44])[C:11]1=[O:12])(=[O:43])[CH2:30][CH2:31][CH2:32][CH2:33][C@H:34]1[C@@H:42]2[C@@H:37]([NH:38][C:39]([NH:41]2)=[O:40])[CH2:36][S:35]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 131724518HCID 131724518, compound

Product 1

HCID 9894791HCID 9894791, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent2×

Procedure

A solution of (R)-1-(5-acetoxyhexyl)-3-(N-biotinyl-6-aminohexyl)-7-methylxanthine (110 mg) in methanol (10 ml) was treated with one drop of concentrated hydrochloric acid solution. After stirring al room temperature for 14 hours, the mixture was treated with 2M solution of ammonia in methanol (3 ml) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 20methano/dichloromethane to provide (R)-3-(N-biotinyl-6-aminohexyl)-1-(5-hydroxyhexyl)-7-methylxanthine (CT12460) (66 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by flash chromatography on silica gel eluting with 20methano/dichloromethane

Sources & evidence

ORD record
ord-d03ddf454a7e404fbdd8935a8d99d61e
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

Loading…