Tetrahydrofuran → Methyl 7-{[4'-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]methylcarbamoyl}heptanoate

HRID 1244646Notes

Reaction equation

HRID 1244646 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]3[S:21][C:20](=[O:22])[NH:19][C:18]3=[O:23])=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1.C1COCC1.C(N(CC)CC)C.Cl[C:37](=[O:48])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([O:46][CH3:47])=[O:45]>O>[O:22]=[C:20]1[NH:19][C:18](=[O:23])[CH:17]([CH2:16][C:13]2[CH:12]=[CH:11][C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([CH2:3][N:2]([CH3:1])[C:37]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([O:46][CH3:47])=[O:45])=[O:48])[CH:5]=3)=[CH:15][CH:14]=2)[S:21]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 4586585Methyl 8-chloro-8-oxooctanoateHCID 120854865-(3'-Methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione

Product 1

HCID 10345737Methyl 7-{[4'-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]methylcarbamoyl}heptanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

600 mg (1.36 mmol) of 5-(3′-methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione, 10 ml of THF and 600 μl (4.3 mmol) of triethylamine are introduced into a round-bottomed flask and under a nitrogen stream. 220 μl (1.55 mmol) of methyl 8-chloro-8-oxooctanoate are added dropwise and the mixture is stirred for one hour. The reaction medium is poured into water, extracted with dichloromethane, the organic phase decanted off, washed with water, dried over magnesium sulphate and evaporated off. The residue obtained is purified by chromatography on a silica column eluted with a dichloromethane and ethyl acetate (80–20) mixture. After evaporation of the solvents, 350 mg (50%) of methyl 7-{[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]methylcarbamoyl}heptanoate are recovered in the form of an oil.

Workup

  1. extractionextracted with dichloromethane
  2. customthe organic phase decanted off
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated off
  6. customThe residue obtained
  7. customis purified by chromatography on a silica column
  8. washeluted with a dichloromethane and ethyl acetate (80–20) mixture
  9. customAfter evaporation of the solvents, 350 mg (50%) of methyl 7-{[4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]methylcarbamoyl}heptanoate
  10. customare recovered in the form of an oil

Sources & evidence

ORD record
ord-6037d9f9a81c48688f1e0aaaca63a3b0
Source dataset
uspto-grants-2006_10
Patent number
US07122564B2

Reaction notes

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