Succinic anhydride → N-{2-[2-(2-tert-butoxycarbonylamino-ethoxy)-ethoxy]-ethyl}-succinamic acid

HRID 535286Notes

Reaction equation

HRID 535286 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][NH2:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]1(=[O:24])[O:23][C:21](=[O:22])[CH2:20][CH2:19]1>>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 7922Succinic anhydrideHCID 9881394tert-butyl N-{2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate

Product 1

HCID 57325707N-{2-[2-(2-tert-butoxycarbonylamino-ethoxy)-ethoxy]-ethyl}-succinamic acidYield 98%

Procedure

Preparation from 1-(t-butyloxycarbonylamino)-3,6-dioxa-8-octanamine) (5 g, 20.16 mmol) and succinic anhydride (2.218 g, 22.18 mmol) gave a thick yellow oil which crystallised on standing (6.5 g, yield 98%). LCMS (Method 6): Rt 2.99 min; m/z (M+1) 349; Calcd.: 349.

Workup

  1. customgave a thick yellow oil which
  2. customcrystallised

Sources & evidence

ORD record
ord-837dc7ab42e54916bd5c33b713465775
Source dataset
uspto-grants-2014_10
Patent number
US08859493B2

Reaction notes

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