Ammonium Hydroxide → N-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl)-3-(tritylthio)propanamide

HRID 1845720Notes

Reaction equation

HRID 1845720 reaction equation
[C:1]1([C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:8][CH2:9][CH2:10][C:11](ON2C(=O)CCC2=O)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:33][CH2:34][CH2:35][O:36][CH2:37][CH2:38][O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][OH:45].[OH-].[NH4+]>ClCCl>[OH:45][CH2:44][CH2:43][O:42][CH2:41][CH2:40][O:39][CH2:38][CH2:37][O:36][CH2:35][CH2:34][NH:33][C:11](=[O:12])[CH2:10][CH2:9][S:8][C:7]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 160103Ethanol, 2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]-HCID 179354262,5-Dioxopyrrolidin-1-yl 3-(tritylthio)propanoate

Product 1

HCID 68927996N-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl)-3-(tritylthio)propanamideYield 82.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Succinimido 3-(triphenylmethylthio)propanoate (4.06 mg, 9.12 mmol) was added to a 0° C. solution of 2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethanol (C. Bertozzi and M. Bednarski, J. Org. Chem. 1991, 56, 4326-4329) (9.12 mmol) in dichloromethane (20 mL). The solution was stirred at room temperature for 2 days and concentrated ammonium hydroxide (1 mL) was added. After 20 minutes, the mixture was filtered and the filtrate was subjected to an extractive workup. The organic layer were dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by HPFC on silica gel (gradient elution with 2-19% CMA in chloroform) to provide 3.95 g of N-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl)-3-(tritylthio)propanamide as a colorless oil.

Workup

  1. waitAfter 20 minutes
  2. filtrationthe mixture was filtered
  3. dry with materialThe organic layer were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by HPFC on silica gel (gradient elution with 2-19% CMA in chloroform)

Sources & evidence

ORD record
ord-2dd8f0e9717841589cc67d31e5e128d2
Source dataset
uspto-grants-2015_02
Patent number
US08951528B2

Reaction notes

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