1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68908937, compound

HRID 2096131Notes

Reaction equation

HRID 2096131 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([NH:15][CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11].[C:17]([O:21][C:22]([CH2:24][NH:25][CH:26]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:27](O)=[O:28])=[O:23])([CH3:20])([CH3:19])[CH3:18].C(N(C(C)C)C(C)C)C.CCN=C=NCCCN(C)C>C1COCC1>[C:17]([O:21][C:22]([CH2:24][NH:25][CH:26]([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:27]([CH2:16][NH:15][CH:9]([CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[I:1])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:28])=[O:23])([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 21896750HCID 21896750, compoundHCID 57741178HCID 57741178, compound

Product 1

HCID 68908937HCID 68908937, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 3-(2-iodophenyl)-2-methylaminopropionate (3.94 g, 12 mmol), 2-(tert-butoxycarbonylmethylamino)-3-phenylpropionic acid (3.7 g, 13 mmol), N-ethyldiisopropylamine (7.8 g, 61 mmol) and EDAC (4.6 g, 24 mmol) were stirred in THF (abs., 50 ml) for 16 h. The reaction solution was concentrated on a rotary evaporator. The residue was taken up in ethyl acetate, washed, dried and concentrated. Purification by column chromatography (SiO2, hexane/ethyl acetate) gave 4.0 g (56%) of the target compound.

Workup

  1. concentrationThe reaction solution was concentrated on a rotary evaporator
  2. washwashed
  3. customdried
  4. concentrationconcentrated
  5. customPurification by column chromatography (SiO2, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5696f2adf1354eb59f40b1c116eae970
Source dataset
uspto-grants-2013_05
Patent number
US08450301B2

Reaction notes

Loading…