Ether hydrochloride → HCID 67230533, compound

HRID 448506Notes

Reaction equation

HRID 448506 reaction equation
[ClH:1].CCOCC.[C:7]([O:11][C:12](=[O:39])[C@@H:13]([N:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[CH2:29][NH:30]C(OC(C)(C)C)=O)[C:20]1=[O:38])[CH2:14][CH2:15][C:16](=[O:18])[NH2:17])([CH3:10])([CH3:9])[CH3:8]>C(Cl)Cl>[ClH:1].[C:7]([O:11][C:12](=[O:39])[C@@H:13]([N:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[CH2:29][NH2:30])[C:20]1=[O:38])[CH2:14][CH2:15][C:16](=[O:18])[NH2:17])([CH3:10])([CH3:8])[CH3:9]

Participants

4

Reactant 2

HCID 10953452Ether hydrochlorideHCID 67229532(2S)-2-[4-(t-butoxycarbonylamino-methyl)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-4-carbamoyl-butyric acid t-butyl ester

Product 1

HCID 67230533HCID 67230533, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2N HCl/ether (14 mL) was added to a stirred solution of (2S)-2-[4-(t-butoxycarbonylamino-methyl)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-4-carbamoyl-butyric acid t-butyl ester (2.5 g, 5.4 mmol) in CH2Cl2 (25 mL). The mixture was stirred for 5 hours. Solid was collected by filtration to give (2S)-2-(4-aminomethyl-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-carbamoyl butyric acid t-butyl ester hydrochloride (2.1 g, 97%): 1H NMR (DMSO-d6) δ 1.37 (s, 9H), 2.08-2.37 (m, 4H), 4.47-4.51 (m, 2H), 4.73-4.79 (dd, J=4.6 and 10.0 Hz, 1H), 6.73 (s, 1H), 7.25 (s, 1H), 7.92-8.03 (m, 3H), 8.68 (s, 3H).

Workup

  1. filtrationSolid was collected by filtration

Sources & evidence

ORD record
ord-7dc33fa6f99f407582ce1bd193fab44e
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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