3-Phthalimidopropionic acid → Tert-butyl 2-(2-(2-(3-(1,3-dioxoisoindolin-2-yl)propanamido)ethoxy)-ethoxy)ethylcarbamate

HRID 1848372Notes

Reaction equation

HRID 1848372 reaction equation
ClC1C=C(CCCNC(=O)/C=C2\OC(C)(C)OC\2=O)C=CC=1Cl.[NH2:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37].[O:41]=[C:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44](=[O:51])[N:43]1[CH2:52][CH2:53][C:54](O)=[O:55]>>[O:41]=[C:42]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:44](=[O:51])[N:43]1[CH2:52][CH2:53][C:54]([NH:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][NH:33][C:34](=[O:40])[O:35][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:55]

Participants

4

Reactant 3

HCID 768593-Phthalimidopropionic acidHCID 9881394tert-butyl N-{2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamateHCID 21947512(Z)-N-(3-(3,4-dichlorophenyl)propyl)-2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-ylidene)acetamide

Product 1

HCID 86728174Tert-butyl 2-(2-(2-(3-(1,3-dioxoisoindolin-2-yl)propanamido)ethoxy)-ethoxy)ethylcarbamateYield 97.3%

Procedure

By appropriate application of the method used to synthesize Intermediate 5, tert-butyl 2-(2-(2-aminoethoxy)ethoxy)ethylcarbamate (400 mg, 1.6 mmol) and 3-(1,3-dioxoisoindolin-2-yl)propanoic acid (388 mg, 1.8 mmol) were combined to provide Intermediate 7A (700 mg, 87% yield). HPLC/MS (Method C) RT=2.80 min, [M+H]+ 450.

Sources & evidence

ORD record
ord-d2bf04ff5ac840daafed1fe504973deb
Source dataset
uspto-grants-2015_02
Patent number
US08952180B2

Reaction notes

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