N-{2-[2-(2-tert-butoxycarbonylamino-ethoxy)-ethoxy]-ethyl}-succinamic acid → 7-(2-{2-[2-(3-Carboxy-propionylamino)-ethoxy]-ethoxy}-ethylcarbamoyl)-heptanoic acid tert-butyl ester

HRID 535288Notes

Reaction equation

HRID 535288 reaction equation
O=C1CCC(=O)N1O[C:9](=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].C(OC([NH:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][NH:40][C:41](=[O:47])[CH2:42][CH2:43][C:44]([OH:46])=[O:45])=O)(C)(C)C>>[C:19]([O:18][C:16](=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9](=[O:23])[NH:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][NH:40][C:41](=[O:47])[CH2:42][CH2:43][C:44]([OH:46])=[O:45])([CH3:20])([CH3:21])[CH3:22]

Participants

3

Reactant 2

HCID 57325707N-{2-[2-(2-tert-butoxycarbonylamino-ethoxy)-ethoxy]-ethyl}-succinamic acidHCID 597608961-tert-Butyl 8-(2,5-dioxopyrrolidin-1-yl) octanedioate

Product 1

HCID 594769997-(2-{2-[2-(3-Carboxy-propionylamino)-ethoxy]-ethoxy}-ethylcarbamoyl)-heptanoic acid tert-butyl esterYield 132.2%

Procedure

Octanedioic acid tert-butyl ester 2,5-dioxo-pyrrolidin-1-yl ester (1.13 g, 3.45 mmol) and N-{2-[2-(2-tert-butoxycarbonylamino-ethoxy)-ethoxy]-ethyl}-succinamic acid (1 g, 2.874 mmol) were reacted as described above. 1.75 g crude product was isolated and used without further purification. LCMS (Method 6): Rt 3.86 min; m/z (M+1) 461; Calcd.: 461.

Sources & evidence

ORD record
ord-2a07b649065546e887f7a4bcd38c2feb
Source dataset
uspto-grants-2014_10
Patent number
US08859493B2

Reaction notes

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