Methanol → 8-(4'-Carboxymethyloxyphenyl)-1,3-dipropylxanthine 2-(biotinylamino)ethylamide

HRID 2309705Notes

Reaction equation

HRID 2309705 reaction equation
[NH2:1][CH2:2][CH2:3][NH-:4].[C:5]([CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[NH:24][C:23]3[C:22](=[O:25])[N:21]([CH2:26][CH2:27][CH3:28])[C:20](=[O:29])[N:19]([CH2:30][CH2:31][CH3:32])[C:18]=3[N:17]=2)=[CH:12][CH:11]=1)([OH:7])=[O:6].O[N:34]1[C:55](=[O:56])[NH:54][C@H:53]2[C@@H:35]1[CH2:36][S:37][C@H:38]2[CH2:39][CH2:40][CH2:41][CH:42](N1C(=O)CCC1=O)[C:43](=[O:45])O.CO.CCOCC>CN(C=O)C>[C:43]([NH:1][CH2:2][CH2:3][NH-:4])(=[O:45])[CH2:42][CH2:41][CH2:40][CH2:39][C@H:38]1[C@@H:53]2[C@@H:35]([NH:34][C:55]([NH:54]2)=[O:56])[CH2:36][S:37]1.[C:5]([CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[NH:24][C:23]3[C:22](=[O:25])[N:21]([CH2:26][CH2:27][CH3:28])[C:20](=[O:29])[N:19]([CH2:30][CH2:31][CH3:32])[C:18]=3[N:17]=2)=[CH:14][CH:15]=1)([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 129676281N-Hydroxysuccinimido-d-biotinHCID 1317152688-(4'-Carboxymethyloxyphenyl)-1,3-dipropyl xanthine 2-aminoethylamide

Product 1

HCID 1317148568-(4'-Carboxymethyloxyphenyl)-1,3-dipropylxanthine 2-(biotinylamino)ethylamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 6d (24.1 mg, 0.056 mmol) was suspended in 1 ml DMF. N-Hydroxysuccinimido-d-biotin (Sigma, 23.6 mg, 0.069 mmol) was added with stirring. A solution formed after several minutes, and a precipitate appeared soon thereafter. After one day methanol (1 ml) and ether were added. The precipitate was collected and dried (yield 26.6 mg, 73%).

Workup

  1. customA solution formed after several minutes
  2. customThe precipitate was collected
  3. customdried (yield 26.6 mg, 73%)

Sources & evidence

ORD record
ord-1fbbfda2c0844ab5a4fb869214c16b2b
Source dataset
uspto-grants-1987_09
Patent number
US04696932

Reaction notes

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