1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86702810, compound

HRID 1525611Notes

Reaction equation

HRID 1525611 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[Na].[CH3:16][CH:17]([C:19]1[N:23]([CH2:24][CH2:25][C@@H:26]([OH:34])[CH2:27][C@@H:28]([OH:33])[CH2:29][C:30](O)=[O:31])[C:22]([C:35]2[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=2)=[C:21]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:20]=1[C:48]([NH:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)=[O:49])[CH3:18].CCN=C=NCCCN(C)C>CC#N.CCOC(C)=O>[F:41][C:38]1[CH:37]=[CH:36][C:35]([C:22]2[N:23]([CH2:24][CH2:25][C@@H:26]([OH:34])[CH2:27][C@@H:28]([OH:33])[CH2:29][C:30]([NH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:31])[C:19]([CH:17]([CH3:18])[CH3:16])=[C:20]([C:48](=[O:49])[NH:50][C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[C:21]=2[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 60823AtorvastatinHCID 5360545SodiumHCID 12106198tert-Butyl [2-(2-aminoethoxy)ethyl]carbamate

Product 1

HCID 86702810HCID 86702810, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-(2-aminoethoxyl)ethylcarbamate (150 mg, 0.735 mmol) is then taken up in CH3CN (10 mL) along with the sodium salt of atorvastatin (0.735 mmol) and EDCI (155 mg, 0.81 mmol). The resulting reaction mixture is stirred at room temperature for 18 h. It is then diluted with EtOAc (20 mL), washed with saturated aqueous NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue is purified by silica gel chromatography (9:1 CH2Cl2/MeOH) to afford tert-butyl 2-(2-((3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanamido)ethoxy)ethylcarbamate.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with saturated aqueous NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel chromatography (9:1 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-bde0e4bf47964993a3027bbca0ffd4b3
Source dataset
uspto-grants-2015_07
Patent number
US09084826B2

Reaction notes

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