Tert-Butylamine → 8-t-BUTYLCARBAMYL-5-(3-(7-CHLOROQUINOLIN-2-YLMETHOXY)PHENYL)-4,6-DITHIAOCTANOIC ACID

HRID 22587Notes

Reaction equation

HRID 22587 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH:20]([S:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[S:21][CH2:22][CH2:23][C:24]([OH:26])=O)[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[I-].ClC1C=CC=C[N+]=1C.[C:49]([NH2:53])([CH3:52])([CH3:51])[CH3:50]>C(Cl)Cl.CC#N>[C:49]([NH:53][C:24]([CH2:23][CH2:22][S:21][CH:20]([C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([O:13][CH2:12][C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=3)[N:9]=2)[CH:15]=1)[S:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[O:26])([CH3:52])([CH3:51])[CH3:50]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 100513215-(3-(7-Chloroquinolin-2-ylmethoxy)phenyl)-4,6-dithianonanedioic acid

Product 1

HCID 199305188-t-BUTYLCARBAMYL-5-(3-(7-CHLOROQUINOLIN-2-YLMETHOXY)PHENYL)-4,6-DITHIAOCTANOIC ACID

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of di-acid (Step 2) (55 g, 0.114 mol.), triethylamine (35 mL), in CH2Cl2 (2.8 l) and CH3CN (500 mL) at 0° was added 2-chloro-1-methylpyridinium iodide (32 g, 0.126 m). The suspension was stirred 1 hr at 0° to afford a yellow solution. To this solution was added t-butylamine (14 mL). The reaction was stirred at room temperature overnight. The mixture was then evaporated, and partitioned between ethyl acetate and H2O. The aqueous phase was adjusted to pH 3-4 before extraction. The organic phase was dried and evaporated. Flash chromatography of the residue using 15% acetone and 0.2% AcOH in toluene afforded the title compound as an oil. Trituration with ethanol afforded the title compound as a white solid which was further purified by swishing in ether.

Workup

  1. customto afford a yellow solution
  2. stirringThe reaction was stirred at room temperature overnight
  3. customThe mixture was then evaporated
  4. custompartitioned between ethyl acetate and H2O
  5. extractionThe aqueous phase was adjusted to pH 3-4 before extraction
  6. customThe organic phase was dried
  7. customevaporated

Sources & evidence

ORD record
ord-1e1e190b0dc84af889d23392fb6ef901
Source dataset
uspto-grants-1995_06
Patent number
US05428171

Reaction notes

Loading…