Hydrochloric Acid → (2-{2-[2-(2-{2-[12-(2-Iodoacetylamino)dodecanoylamino]ethoxy}ethoxy)acetylamino]ethoxy}-ethoxy)acetic acid

HRID 593237Notes

Reaction equation

HRID 593237 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][C:9]([NH:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][C:19]([OH:21])=[O:20])=[O:10].O=C1CCC(=O)N1[O:29][C:30](=O)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][NH:42][C:43](=[O:46])[CH2:44][I:45].Cl>C(=O)([O-])[O-].[Na+].[Na+].C(#N)C>[I:45][CH2:44][C:43]([NH:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][C:30]([NH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][C:9]([NH:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][C:19]([OH:21])=[O:20])=[O:10])=[O:29])=[O:46]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 5134091817-Amino-10-oxo-3,6,12,15-tetraoxa-9-azaheptadecanoic acidHCID 8665101612-(2-Iodoacetylamino)dodecanoic acid 2,5-dioxopyrrolidin-1-yl ester

Product 1

HCID 86651015(2-{2-[2-(2-{2-[12-(2-Iodoacetylamino)dodecanoylamino]ethoxy}ethoxy)acetylamino]ethoxy}-ethoxy)acetic acidYield 49%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 10340Sodium CarbonateSolvent

Procedure

To a solution of [2-(2-{2-[2-(2-aminoethoxy)ethoxy]acetylamino}ethoxy)ethoxy]acetic acid (194 mg) in 0.1 M sodium carbonate was added acetonitrile (5 ml) followed by a solution of 12-(2-Iodoacetylamino)dodecanoic acid 2,5-dioxopyrrolidin-1-yl ester (260 mg) in acetonitrile (6 ml). After stirring for 45 min, pH was adjusted to 4 with 1 N HCl and the mixture was purified by preparative HPLC: C18, 3 cm column (Gemini), A-buffer 0.1% TFA in MiliQ water, B-buffer: 0.1% TFA in AcCN, flow 20 ml/min, gradient 10-80% B over 30 min. Product containing fractions were pooled and concentrated to give the title compound in 49% yield (180 m). LC-MS, M/z: 674.3 (M+1).

Workup

  1. customthe mixture was purified by preparative HPLC
  2. customover 30 min
  3. additionProduct containing fractions
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5f8af9b56d2a4f5da3ae46130df9a3af
Source dataset
uspto-grants-2016_01
Patent number
US09242011B2

Reaction notes

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