1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22844257, compound

HRID 1197002Notes

Reaction equation

HRID 1197002 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:33](O)=[O:34])[C:10]([S:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.Cl.[CH2:58]([O:60][C:61](=[O:64])[CH2:62][NH2:63])[CH3:59]>C(Cl)(Cl)Cl.O1CCCC1.O.C(N(CC)CC)C>[CH2:58]([O:60][C:61](=[O:64])[CH2:62][NH:63][C:33](=[O:34])[C@H:9]([C:10]([S:13][C:14]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([CH3:12])[CH3:11])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:59]

Participants

9

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2723640Glycine ethyl ester, hydrochlorideHCID 15000273N-(tert-Butoxycarbonyl)-3-[(triphenylmethyl)sulfanyl]-L-valine

Product 1

HCID 22844257HCID 22844257, compoundYield 99%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6212ChloroformSolvent2×HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To the solution of N-t-butoxycarbonyl-S-trityl-L-penicillamine (A-1) (4.0 g) and 1-hydroxybenzotriazole (abbreviated as HOBt) (1.2 g) in chloroform (40 ml) and tetrahydrofuran (16 ml), was added dropwise by ice-cooling the solution of 1-ethyl-3-(3dimethylaminopropyl)carbodiimide (water-soluble carbodiimide: abbreviated as WSC) (1.7 g) in chloroform (10 ml). The mixture was stirred at the same temperature for 1 hour, then glycine ethyl ester hydrochloride (1.1 g) and triethylamine (0.85 ml) were added, and the mixture was stirred at room temperature for 12 hours. After addition of water, the organic layer was washed with an aqueous solution of potassium hydrogensulfate, water, an aqueous solution of sodium hydrogencarbonate, water and saturated saline, in this order, and dried over magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was subjected to column chromatography, to give N-t-butoxycarbonyl-S-trityl-L-penicillamylglycine ethyl ester (4.5 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. washthe organic layer was washed with an aqueous solution of potassium hydrogensulfate, water
  3. dry with materialan aqueous solution of sodium hydrogencarbonate, water and saturated saline, in this order, and dried over magnesium sulfate
  4. customThe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-f6d32edeb5b5411fa6745c530055f91b
Source dataset
uspto-grants-1992_05
Patent number
US05116861

Reaction notes

Loading…