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

HRID 65003Notes

Reaction equation

HRID 65003 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[NH:20][C:19]3[C:18](=[O:21])[N:17]([CH2:22][CH2:23][CH3:24])[C:16](=[O:25])[N:15]([CH2:26][CH2:27][CH3:28])[C:14]=3[N:13]=2)=[CH:8][CH:7]=1)([OH:3])=[O:2].O[N:30]1[C:51](=[O:52])[NH:50][C@H:49]2[C@@H:31]1[CH2:32][S:33][C@H:34]2[CH2:35][CH2:36][CH2:37][CH:38](N1C(=O)CCC1=O)[C:39](=[O:41])O.CO.CCOCC>CN(C=O)C>[C:39]([NH:13][CH2:14][CH2:19][NH-:20])(=[O:41])[CH2:38][CH2:37][CH2:36][CH2:35][C@H:34]1[C@@H:49]2[C@@H:31]([NH:30][C:51]([NH:50]2)=[O:52])[CH2:32][S:33]1.[C:1]([CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[NH:20][C:19]3[C:18](=[O:21])[N:17]([CH2:22][CH2:23][CH3:24])[C:16](=[O:25])[N:15]([CH2:26][CH2:27][CH3:28])[C:14]=3[N:13]=2)=[CH:10][CH:11]=1)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 1260798-(4-Carboxymethyloxy)phenyl-1,3-dipropylxanthineHCID 129676281N-Hydroxysuccinimido-d-biotin

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-eb793162060e4d608a6c1a06068b387a
Source dataset
uspto-grants-1986_09
Patent number
US04612315

Reaction notes

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