Tetrabutylammonium Fluoride → HCID 54325888, compound

HRID 975965Notes

Reaction equation

HRID 975965 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]=[C:15]([OH:19])[CH:14]=2)[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]=[C:15]([OH:19])[CH:14]=2)[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 53675328HCID 53675328, compound

Product 1

HCID 54325888HCID 54325888, compoundYield 19.5%

Procedure

The operation is carried out in a fashion similar to that described in Example 41, but starting from 4.0 g of 2-trimethylsilylethyl (2R,4R)-3-{3-{2-[4-tert-butoxycarbonyl-2-(3-hydroxyphenyl)-3-thiazolidinyl]-2-oxoethyl}ureido}benzoate and 11.8 cm3 of 1M tetrabutylammonium fluoride solution. The crude product is purified by chromatography on silica [eluent: ethyl acetate]. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure at 40° C. The solid residue is dissolved in 8.0 cm3 of a 0.5N aqueous sodium hydroxide solution. The solution is filtered and acidified with 4.1 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. 0.65 g of (2R,4R)-3-{3-{2-[4-tert-butoxycarbonyl-2-(3-hydroxyphenyl)-3-thiazolidinyl]-2-oxoethyl}ureido}-benzoic acid, melting at 150° C., is thus obtained. ([α]D20 =+62°±2° (C=0.28%; DMF)) [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.: 6.8 (bd, 1H, O--C6H4 --C in position 4; 7.0 to 7.6 (m, 6H, aromatic); 8.0 (bs, 1H, N--C6H4 -- in position 2). Infrared spectrum (KBr), characteristic bands in cm-1 : 3380, 2975, 2930, 2625, 1700, 1650, 1590, 1560, 1490, 1370, 1235, 1150, 785, 760, 690, 680].

Workup

  1. customThe crude product is purified by chromatography on silica [eluent: ethyl acetate]
  2. additionThe fractions containing the expected product
  3. concentrationconcentrated to dryness under reduced pressure at 40° C
  4. dissolutionThe solid residue is dissolved in 8.0 cm3 of a 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-d5aaa43af5de47cc900484c39d184db5
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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