Ammonia → HCID 9894791, compound

HRID 1835741Notes

Reaction equation

HRID 1835741 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 at 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 20% methanol/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 20% methanol/dichloromethane

Sources & evidence

ORD record
ord-7ea844648d4b40c89b04a42a501b80b4
Source dataset
uspto-grants-2004_08
Patent number
US06774130B2

Reaction notes

Loading…