Propargylamine → 6-((6-((Biotinoyl)amino)hexanoyl)amino)hexanoyl propargyl amine

HRID 1595930Notes

Reaction equation

HRID 1595930 reaction equation
[C:1]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32]N1C(=O)CCC1=O)=O)=[O:23])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C@@H:14]2[C@@H:9]([NH:10][C:11]([NH:13]2)=[O:12])[CH2:8][S:7]1.[CH2:40]([NH2:43])[C:41]#[CH:42]>CN(C=O)C>[C:1]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([NH:43][CH2:40][C:41]#[CH:42])=[O:32])=[O:23])(=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[C@@H:14]2[C@@H:9]([NH:10][C:11]([NH:13]2)=[O:12])[CH2:8][S:7]1

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 16219024N-(6-((2,5-Dioxopyrrolidin-1-yl)oxy)-6-oxohexyl)-6-((5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno(3,4-d)imidazol-4-yl)pentanoyl)amino)hexanamide

Product 1

HCID 882348336-((6-((Biotinoyl)amino)hexanoyl)amino)hexanoyl propargyl amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-((6-((Biotinoyl)amino)hexanoyl)amino)hexanoic acid, succinimidyl ester (biotin-NHS ester) (0.2 g, 0.35 mmol) in dry DMF (5 ml), propargyl amine (0.04 ml, 0.6 mmol) was added. A white precipitate formed within 15 min and the mixture was stirred overnight. The solvent was removed in vacuo and the compound was dissolved in CHCl3. Next the CHCl3 was slowly added to a stirred solution of hexane, forming a white precipitate, which on drying afforded 0.15 g (83%). Mass Spect. (FAB) MW 508 [M+]; NMR assigned. Crisp, G. T.; Gore, J. Syn. Comm. 1997, 27, 2203-2125

Workup

  1. customA white precipitate formed within 15 min
  2. customThe solvent was removed in vacuo
  3. dissolutionthe compound was dissolved in CHCl3
  4. additionNext the CHCl3 was slowly added to a stirred solution of hexane
  5. customforming a white precipitate, which
  6. customon drying
  7. customafforded 0.15 g (83%)

Sources & evidence

ORD record
ord-6d03c2dcbfae449498fd9071af32762a
Source dataset
uspto-grants-2001_09
Patent number
US06288221B1

Reaction notes

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