4-(Iodomethyl)oxane → HCID 21094183, compound

HRID 729712Notes

Reaction equation

HRID 729712 reaction equation
[C:1]([O:5][C:6]([CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[CH2:20][CH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>>[C:1]([O:5][C:6]([CH:8]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:17][CH:18]=1)[CH2:20][CH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 27955074-(Iodomethyl)oxaneHCID 154164151,1-Dimethylethyl 4-(methoxycarbonyl)benzeneacetate

Product 1

HCID 21094183HCID 21094183, compound

Procedure

Methyl 4-tert-butoxycarbonylmethylbenzoate (1.71 g, 6.84 mmol) was alkylated with 4-iodomethyltetrahydropyran (1.86 g, 8.21 mmol), employing the method described in Preparation 41, to afford methyl 4-[1-tert-butoxycarbonyl-2-(tetrahydropyran-4-yl)ethyl]benzoate: RTA=3.86 min. A solution of this compound (1.37 g, 3.94 mmol) in CH2Cl2 (5 mL) was treated with TFA-CH2Cl2 (2:1, 15 mL) at 0° C. over 10 min. The mixture was stirred at 20° C. for 3 h, before being concentrated in vacuo. The residue was treated with PhMe and the solvents were evaporated off under reduced pressure. This process was repeated twice to provide crude methyl 4-[1-carboxy-2-(tetrahydropyran-4-yl)ethyl]benzoate. This carboxylic acid was condensed with thiazol-2-ylamine, utilizing the protocol outlined in EXAMPLE 65, to furnish methyl 4-[2-(tetrahydropyran-4-yl)-1-(thiazol-2-ylcarbamoyl)ethyl]benzoate: m/z (ES+)=375.2 [M+H]+. This ester (1.20 g, 3.21 mmol) was saponified with LiOH.H2O, using the procedure described in Preparation 22, to furnish the title compound: m/z (ES−)=359.2 [M−H]−.

Workup

  1. customdescribed in Preparation 41

Sources & evidence

ORD record
ord-d4771b2e43e6488992a07ee9b149738a
Source dataset
uspto-grants-2009_09
Patent number
US07582632B2

Reaction notes

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