Water → HCID 68161901, compound

HRID 1472987Notes

Reaction equation

HRID 1472987 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[CH2:14]Cl)=[O:4].C(N([CH2:22][CH3:23])CC)C.[CH2:24]([O:31][CH2:32][C:33]([OH:35])=[O:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[OH2:36]>CC(C)=O>[CH2:24]([O:31][CH2:32][C:33]([O:35][CH2:2][C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([CH2:14][O:36][C:33](=[O:34])[CH2:32][O:31][CH2:24][C:23]1[CH:22]=[CH:27][CH:26]=[CH:25][CH:30]=1)=[O:16])=[O:4])=[O:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 290301(Benzyloxy)acetic acidHCID 4591685ST51021581

Product 1

HCID 68161901HCID 68161901, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-Chloro-N-[6-(2-chloro-acetylamino)-hexyl]-acetamide (200 gm) and triethyl amine (400 ml) in Acetone (2000 ml) at room temperature was added dropwise Benzyloxy acetic acid (350 g). The solution was further stirred at reflux temperature overnight. The reaction mixture was poured onto cold water and solids were filtered, dried and the crude product was purified by recrystallisation from Ethyl acetate to yield pure (Benzyloxy-acetic acid-{6-[2-(2-benzyloxy-acetoxy)-acetylamino]-hexylcarbamoyl}-methyl ester) (190 g) as white powder with a melting point of 101-103° C. The product was characterized by 1H NMR (CDCl3+DMSO-d3) δ 1.24 (m, 2H, CH2), 1.43 (m, 2H, CH2), 3.15 (t, 2H, CH2), 4.15 (s, 2H, CH2), 4.48 (s, 2H, CH2), 4.56 (s, 2H, CH2), 7.30 (m, 5H, Ar), 7.46 (t, 1H, NH).

Workup

  1. temperatureat reflux temperature overnight
  2. filtrationwere filtered
  3. customdried
  4. customthe crude product was purified by recrystallisation from Ethyl acetate

Sources & evidence

ORD record
ord-ee8ff3d7452c43789c6e33f80fd1af2f
Source dataset
uspto-grants-2015_04
Patent number
US09012677B2

Reaction notes

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