Tetrabutylammonium Fluoride → HCID 9957029, compound

HRID 975966Notes

Reaction equation

HRID 975966 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][CH:14]=2)[N:9]1[C:19](=[O:40])[CH2:20][NH:21][C:22](=[O:39])[NH:23][C:24]1[CH:25]=[C:26]([CH:36]=[CH:37][CH:38]=1)[C:27]([O:29]CC[Si](C)(C)C)=[O:28])=[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:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:9]1[C:19](=[O:40])[CH2:20][NH:21][C:22](=[O:39])[NH:23][C:24]1[CH:25]=[C:26]([CH:36]=[CH:37][CH:38]=1)[C:27]([OH:29])=[O:28])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53653205HCID 53653205, compound

Product 1

HCID 9957029HCID 9957029, compoundYield 30.6%

Procedure

The operation is carried out in a fashion similar to that described in Example 41, but starting from 1.3 g of 2-trimethylsilylethyl (2R,4R)-3-{3-[2-(4-tert-butoxycarbonyl-2-phenyl-3-thiazolidinyl)-2-oxoethyl]ureido}benzoate and 4.5 cm3 of a molar tetrabutylammonium fluoride solution. The crude product is purified by chromatography on silica [eluent: ethyl acetate/methanol (95/5 by volume)]. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure at 40° C. The solid residue is dissolved in 4.0 cm3 of 0.5N aqueous sodium hydroxide solution. The solution is filtered, and acidified with 2.1 cm3 of a 1N aqueous hydrochloric acid solution. The insoluble product is separated by filtration, washed with 2 times 5 cm3 of water and dried in air. 0.33 g of (2R,4R)-3-{3-[2-(4-tert-butoxycarbonyl-2-phenyl-3-thiazolidinyl)-2-oxoethyl]ureido}benzoic acid, melting at 134° C., is thus obtained. ([α]D20 =+85°±3° (C=0.40%; CHCl3)) [proton NMR (250 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 7.7 (m, 8H, aromatic); 8.0 (bs, 1H, N--C6H4 --C in position 2). Infrared spectrum (KBr), characteristic bands in cm-1 : 3380, 2980, 2930, 2600, 1690, 1650, 1610, 1590, 1555, 1490, 1370, 1235, 1150, 760, 730, 700, 680].

Workup

  1. customThe crude product is purified by chromatography on silica [eluent: ethyl acetate/methanol (95/5 by volume)]
  2. additionThe fractions containing the expected product
  3. concentrationconcentrated to dryness under reduced pressure at 40° C
  4. dissolutionThe solid residue is dissolved in 4.0 cm3 of 0.5N aqueous sodium hydroxide solution
  5. filtrationThe solution is filtered
  6. customThe insoluble product is separated by filtration
  7. washwashed with 2 times 5 cm3 of water
  8. customdried in air

Sources & evidence

ORD record
ord-42868cdc41d941e4b010c67977c4aed1
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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