1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-[2-(3-Benzyloxycarbonylamino-propionylamino)-3-(2-ethoxycarbonyl-ethoxy)-2-(2-ethoxycarbonylethoxymethyl)-propoxy]-propionic acid ethyl ester

HRID 249624

Reaction equation

HRID 249624 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][CH2:6][O:7][CH2:8][C:9]([NH2:28])([CH2:19][O:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:10][O:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:2].[C:30]([NH:40][CH2:41][CH2:42][C:43](O)=[O:44])([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31].C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][CH2:12][O:11][CH2:10][C:9]([NH:28][C:43](=[O:44])[CH2:42][CH2:41][NH:40][C:30]([O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:31])([CH2:19][O:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:8][O:7][CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:29])[CH3:18]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 75313N-Benzyloxycarbonyl-beta-alanineHCID 117325743-[2-Amino-3-(2-ethoxycarbonyl-ethoxy)-2-(2-ethoxycarbonyl-ethoxymethyl)-propoxy]-propionic acid ethyl ester

Product 1

HCID 692966123-[2-(3-Benzyloxycarbonylamino-propionylamino)-3-(2-ethoxycarbonyl-ethoxy)-2-(2-ethoxycarbonylethoxymethyl)-propoxy]-propionic acid ethyl esterYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The compound 23 was prepared using General Procedure B with amine 1 (4.0 g, 9.49 mmol), N-Cbz-β-alanine (2.54 g, 11.39 mmol), 1-hydrobenzotriazole (HOBt) (1.53 g, 11.39 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) (2.18 g, 11.39 mmol) in CH2Cl2 (50 mL). Purification by flash column chromatography (on silica gel, EtOAc:n-hexane=1:3) afforded 5.36 g (90%) of the desired product 23 as a colorless syrup. 1H NMR (CDCl3): δ 7.31 (m, 5H, ArH), 6.16 (s, 1H, NH), 5.66 (s, 1H, NH), 5.08 (s, 2H, OCH2Ar), 4.12 (q, J=6.4 Hz, 6H, OCH2), 3.67 (m, 12H, CH2O), 3.45 (dt, J=7.4, 15.0 Hz, 2H, CH2NHCO), 2.51 (t, J=8.4 Hz, 6H, CH2CO), 2.37 (dt, J=7.4, 8.6 Hz, 2H CH2CO), 1.24 (t, J=6.4 Hz, 9H, CH3).

Workup

  1. customThe compound 23 was prepared
  2. customPurification by flash column chromatography (on silica gel, EtOAc:n-hexane=1:3)

Sources & evidence

ORD record
ord-53737a31a5b7431ca8b92aa627d4b0ca
Source dataset
uspto-grants-2011_01
Patent number
US07862807B2

Linked notes

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