HCID 86750534, compound → HCID 54329938, compound

HRID 975968Notes

Reaction equation

HRID 975968 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[CH2:12][S:11][C@H:10]([C:13]2[CH:14]=[N: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]([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]=[N: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 1

HCID 86750534HCID 86750534, compound

Product 1

HCID 54329938HCID 54329938, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

The operation is carried out in a fashion similar to that described in Example 41, but starting from 0.95 g of 2-trimethylsilylethyl (2R,4R)-3-{3-{2-[4-tert-butoxycarbonyl-2-(3-pyridyl)-3-thiazolidinyl]-2-oxoethyl}ureido}benzoate in 3.2 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. After vigorous stirring in diisopropyl ether, 0.36 g of (2R,4R)-3-{3-{2-[4-tert-butoxycarbonyl-2-(3-pyridyl)-3-thiazolidinyl]-2-oxoethyl}ureido}benzoic acid, melting at 147° C., is thus obtained ([α]D20 =+51.1°±17° (C=0.49%; 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.: 7.3 to 7.6 (m, 5H, aromatic); 8.0 (bs, 1H, N--C6H4 --C in position 2); 8.5 (bs, 1H, H in position 2 of pyridyl); 8.8 (bs, 1H, H in position 6 of pyridyl). Infrared spectrum (KBr), characteristic bands in cm-1 : 3385, 2975, 2930, 2600, 2500, 1730, 1660, 1610, 1590, 1560, 1485, 1370, 1240, 1150, 760, 710, 685].

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

Sources & evidence

ORD record
ord-0d5873f8952a4696980efa5c9e8e91cd
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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