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

HRID 574063Notes

Reaction equation

HRID 574063 reaction equation
[OH:1][C:2]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:51])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36](=[O:50])[CH2:37][CH2:38][CH2:39][CH2:40][CH:41]2[CH:48]3[CH:44]([NH:45][C:46](=[O:49])[NH:47]3)[CH2:43][S:42]2)[CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.C(N=C=NC(C)C)(C)C.O[N:62]1[C:66](=[O:67])[CH2:65][CH2:64][C:63]1=[O:68]>CN(C=O)C>[C:63]1(=[O:68])[N:62]([O:8][C:7](=[O:9])[C:6]2[CH:5]=[CH:4][C:3]([C:2]([OH:1])([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:51])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:36](=[O:50])[CH2:37][CH2:38][CH2:39][CH2:40][CH:41]4[CH:48]5[CH:44]([NH:45][C:46](=[O:49])[NH:47]5)[CH2:43][S:42]4)[CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:11][CH:10]=2)[C:66](=[O:67])[CH2:65][CH2:64]1

Participants

5

Reactant 3

HCID 12734DiisopropylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 726151064-{Hydroxy-[3-(3-{6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-hexanoylamino}-propoxy)-phenyl]-phenyl-methyl}-benzoic acid

Product 1

HCID 726150884-{Hydroxy-[3-(3-{6-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-hexanoylamino}-propoxy)-phenyl]-phenyl-methyl}-benzoic acid succinimidyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of biotinylated trityl acid (5, 175 mg, 0.244 mM) in anhydrous DMF (3 mL) was added 1,3-diisopropyl carbodiimide (4 mg, 0.35 mM) and stirred the reaction mixture for 5 min. To this reaction mixture was added N-hydroxy succinimide (40 mg, 0.32 mM) and stirred for over night at room temperature. The solvent was removed under high vacuum and the residue obtained was purified by silca gel column chromatography using CH3OH/CH2Cl2, 3:7) mixture as a solvent system. Evaporation of the solvent gave 6 as a white crystalline solid. Yield: 80 mg (41%). 1H-NMR (CD3OD) δ ppm:

Workup

  1. stirringstirred for over night at room temperature
  2. customThe solvent was removed under high vacuum
  3. customthe residue obtained
  4. customwas purified by silca gel column chromatography
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-34a584a8ec6742e7a91d12a71b487e5e
Source dataset
uspto-grants-2015_05
Patent number
US09034798B2

Reaction notes

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