Methylparaben → Methyl 4-(3-tert-butoxycarbonyl-4-thiazolidinyl)methoxybenzoate

HRID 350521Notes

Reaction equation

HRID 350521 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11](CO)[S:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1.[CH:26]1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH:12]([CH2:26][O:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:24][CH:25]=2)[CH2:11][S:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 7456MethylparabenHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 235121323-Tert-butoxycarbonyl-5-hydroxymethylthiazolidine

Product 1

HCID 23512106Methyl 4-(3-tert-butoxycarbonyl-4-thiazolidinyl)methoxybenzoateYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-tert-butoxycarbonyl-5-hydroxymethylthiazolidine (1.9 g, 8.7 mmol), methyl 4-hydroxybenzoate (1.3 g, 8.7 mmol), and Ph3P (3.2 g, 12.2 mmol) in THF (10 ml) was added DIAD (2.2 g, 10.4 mmol) at 0° C. The reaction mixture was stirred at room temperature for 18 hr. The mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel with EtOAc-n-hexane (1:9, v/v) as eluent to give methyl 4-(3-tert-butoxycarbonyl-4-thiazolidinyl)methoxybenzoate (1.6 g, 52%) as a pale yellow oil. 1H-NMR (CDCl3) δ 1.49 (s, 9H), 3.11–3.19 (m, 2H), 3.88 (s, 3H), 4.04–4.31 (m, 3H), 4.61 (m, 2H), 6.96 (d, J=8.8 Hz, 2H), 7.98 (d, J=8.8 Hz, 2H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography on silica gel with EtOAc-n-hexane (1:9, v/v) as eluent

Sources & evidence

ORD record
ord-3540b94f2f8c45d08563849ea59defdc
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

Loading…