Dicyclohexylcarbodiimide → HCID 86746314, compound

HRID 373293Notes

Reaction equation

HRID 373293 reaction equation
[C:1]([CH2:9][C:10]([NH:12][CH2:13][C:14]([NH:16][CH2:17][C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])=[O:15])=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.O[N:41]1[C:45](=[O:46])[CH2:44][CH2:43][C:42]1=[O:47]>CN(C)C=O>[C:1]([CH2:9][C:10]([NH:12][CH2:13][C:14]([NH:16][CH2:17][C:18]([NH:20][CH2:21][C:22]([O:24][N:41]1[C:45](=[O:46])[CH2:44][CH2:43][C:42]1=[O:47])=[O:23])=[O:19])=[O:15])=[S:11])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 19780620HCID 19780620, compound

Product 1

HCID 86746314HCID 86746314, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.0 g of (2-benzoylthioacetyl)glycylglycylglycine (2.72 mmol) in 10 mL of dimethylforamide was added 0.56 g of dicyclohexylcarbodiimide (2.72 mmol) and 0.31 g of N-hydroxysuccinimide (2.72 mmol). The solution was stirred at room temperature for 24 hours. The resultant white solid was filtered off. The solvent was removed from the filtrate by rotary evaporator (vacuum pump, 35.) to give the product as a yellow semisolid. This solid was dried under vacuum overnight. The product was then recrystallized from 100 mL of hot 2-propanol to give 0.27 g of a white powder after filtration and drying under vacuum (21%). NMR (DMSO-d6)δ 2.81 (s, 4H), 3.79 (m, integral obscured by water), 3.89 (s, integral obscured by water), 4.28 (d, 2H), 7.58 (d, 2H), 7.71 (t, 1H), 7.93 (d,2H), 8.29 (br t, 1H), 8.54 (m, 2H).

Workup

  1. filtrationThe resultant white solid was filtered off
  2. customThe solvent was removed from the filtrate by rotary evaporator (vacuum pump, 35.)

Sources & evidence

ORD record
ord-363282513e0b44a7bee005e9856048b6
Source dataset
uspto-grants-1992_11
Patent number
US05162505

Reaction notes

Loading…