Dicyclohexylcarbodiimide → HCID 178520597, compound

HRID 2403083Notes

Reaction equation

HRID 2403083 reaction equation
[C-:1]1([CH2:6][NH2:7])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[Fe+2:13].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[SH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][C:50](O)=[O:51]>CC(C)=O>[C-:1]1([CH2:6][NH:7][C:50](=[O:51])[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][SH:39])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:8]1[CH:12]=[CH:11][CH:10]=[CH:9]1.[Fe+2:13]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 54350211-Mercaptoundecanoic AcidHCID 15412229HCID 15412229, compound

Product 1

HCID 178520597HCID 178520597, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 4 (0.175 g, 0.81 mmol), N,N′-dicyclohexylcarbodiimide (0.169 g, 0.82 mmol), 1-hydroxybenzotriazole (0.126 g, 0.82 mmol), and 11-mercaptoundecanoic acid (0.179 g, 0.82 mmol) were combined in degassed acetone (12 mL). The solution was stirred at r.t. for 18 h under an atmosphere of Ar. The reaction mixture was concentrated in vacuo and dissolved in dichloromethane (100 mL). After washing with water (3×50 mL), the organic phase was dried over Na2SO4, filtered, and concentrated to a crude residue that was purified by column chromatography on silica gel (2:3, EtOAc:hexanes) to yield the pure product as a pale orange solid (0.288 g, 0.69 mmol, 85%). 1H NMR (CDCl3): δ 1.25-1.38 (m, 13H, (CH2)6+SH), 1.57-1.66 (m, 4H, COCH2CH2+CH2CH2SH) 2.17 (t, JH-H=7.8 Hz, 2H, COCH2), 2.51 (psuedo dt, JN-H=7.3 Hz, 7.4 Hz, 2H, CH2SH), 4.13-4.15 (m, 4H, NHCH2+ferrocene-H), 4.16 (bs, 5H, ferrocene-H), 4.18 (pt, 2H, ferrocene-H), 5.56 (bs, 1H, NH). 13C{1H} NMR (CDCl3): δ 24.9, 26.0, 28.6, 29.2, 29.5, 29.5, 29.6, 29.6, 34.2, 37.0, 39.0, 68.4, 68.5, 68.8, 85.0, 172.6.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in dichloromethane (100 mL)
  3. washAfter washing with water (3×50 mL)
  4. dry with materialthe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to a crude residue that
  7. customwas purified by column chromatography on silica gel (2:3, EtOAc:hexanes)

Sources & evidence

ORD record
ord-9a9e4952a9a94b28baa6f7162b89bbf4
Source dataset
uspto-grants-2014_08
Patent number
US08802390B2

Reaction notes

Loading…