Biotin-X-NHS → 4-{Hydroxy-[3-(3-{6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-hexanoylamino}-propoxy)-phenyl]-phenyl-methyl}-benzoic acid

HRID 574062Notes

Reaction equation

HRID 574062 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([C:12]([OH:28])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[CH:9]=[CH:10][CH:11]=1.C1C(=O)N([O:36][C:37]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][NH:44][C:45]([CH2:47][CH2:48][CH2:49][CH2:50][CH:51]2[S:55][CH2:54][CH:53]3[NH:56][C:57]([NH:59][CH:52]23)=[O:58])=[O:46])=O)C(=O)C1>CN(C=O)C.CO.C(Cl)(Cl)Cl>[OH:28][C:12]([C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][NH:1][C:37](=[O:36])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][NH:44][C:45](=[O:46])[CH2:47][CH2:48][CH2:49][CH2:50][CH:51]2[CH:52]3[CH:53]([NH:56][C:57](=[O:58])[NH:59]3)[CH2:54][S:55]2)[CH:7]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 5063989Biotin-X-NHSHCID 599879594-{[3-(3-Amino-propoxy)-phenyl]-hydroxy-phenyl-methyl}-benzoic acid

Product 1

HCID 726151064-{Hydroxy-[3-(3-{6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-hexanoylamino}-propoxy)-phenyl]-phenyl-methyl}-benzoic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584188Chloroform methanolSolvent

Procedure

A mixture of Trityl amino acid (4, 100 mg, 0.26 mM) and Biotin-X-NHS (113 mg, 0.25 mM) was stirred at room temperature in 3 mL of anhydrous DMF for overnight. After that DMF was removed under high vacuum and the residue obtained was passed through silica gel column using 50% CH3OH/CHCl3 as a solvent. Evaporation of the solvent yielded biotinylated trityl acid 5. (97.8%). Mass: 739 (M Na+), 715 (M-H).

Workup

  1. customAfter that DMF was removed under high vacuum
  2. customthe residue obtained
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e9fe858c7db44546a6e712365513cc1f
Source dataset
uspto-grants-2015_05
Patent number
US09034798B2

Reaction notes

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