Tetrabutylammonium Fluoride → HCID 54535988, compound

HRID 975964Notes

Reaction equation

HRID 975964 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][S:11][C@H:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[N:9]1[C:20](=[O:41])[CH2:21][NH:22][C:23](=[O:40])[NH:24][C:25]1[CH:26]=[C:27]([CH:37]=[CH:38][CH:39]=1)[C:28]([O:30]CC[Si](C)(C)C)=[O:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][S:11][C@H:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[N:9]1[C:20](=[O:41])[CH2:21][NH:22][C:23](=[O:40])[NH:24][C:25]1[CH:26]=[C:27]([CH:37]=[CH:38][CH:39]=1)[C:28]([OH:30])=[O:29])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 54393558HCID 54393558, compound

Product 1

HCID 54535988HCID 54535988, compoundYield 38.8%

Procedure

The operation is carried out in a fashion similar to that described in Example 41, but starting from 2.0 g of 2-trimethylsilylethyl (2R,4R)-3-{3-{2-[4-tert-butoxycarbonyl-2-(2-chlorophenyl)-3-thiazolidinyl]-2-oxoethyl}ureido}benzoate and 6.5 cm3 of 1M tetrabutylammonium fluoride solution. The crude product is purified by chromatography on silica [eluent: ethyl 0.65 g of acetate/methanol (90/10 by volume)]. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure at 40° C. After vigorous stirring in diisopropyl ether, 0.65 g of (2R,4R)-3-{3-{2-[4-tert-butoxycarbonyl-2-(2-chlorophenyl)-3-thiazolidinyl]-2-oxoethyl}ureido}benzoic acid is thus obtained in the form of an amorphous solid ([α]D20 =+88°±2° (C=0.39%; CHCl3)) [proton NMR (200 MHz, DMSO D6, δ in ppm), 2 rotamers at room temperature, peak coalescence at 120° C., characteristic chemical shifts at 120° C.: 7.3 to 7.6 (m, 7H, aromatic); 7.95 (bs, 1H, N--C6H4 -- in position 2). Infrared spectrum (KBr), characteristic bands in cm-1 : 3390, 2985, 2940, 2600, 1735, 1660, 1610, 1560, 1375, 1240, 1155, 755, 685].

Workup

  1. customThe crude product is purified by chromatography on silica [eluent: ethyl 0.65 g of acetate/methanol (90/10 by volume)]
  2. additionThe fractions containing the expected product
  3. concentrationconcentrated to dryness under reduced pressure at 40° C

Sources & evidence

ORD record
ord-6214d398483b4cfe829fd6dad43f1847
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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