Lithium Hydroxide → HCID 53747184, compound

HRID 975970Notes

Reaction equation

HRID 975970 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:38])[CH2:20][NH:21][C:22](=[O:37])[NH:23][C:24]1[CH:25]=[C:26]([CH:34]=[CH:35][CH:36]=1)[O:27][CH2:28][C:29]([O:31]CC)=[O:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>>[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:38])[CH2:20][NH:21][C:22](=[O:37])[NH:23][C:24]1[CH:25]=[C:26]([CH:34]=[CH:35][CH:36]=1)[O:27][CH2:28][C:29]([OH:31])=[O:30])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 53965662HCID 53965662, compound

Product 1

HCID 53747184HCID 53747184, compoundYield 57.1%

Procedure

The operation is carried out in a fashion similar to that described in Example 39, but starting from 2.4 g of ethyl (2R,4R)-3-{3-[2-(4-tert-butoxycarbonyl-2-phenyl-3-thiazolidinyl)-2-oxoethyl]ureido}phenoxyacetate and 0.2 g of lithium hydroxide. 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, 1.3 g of (2R,4R)-3-{3-[2-(4-tert-butoxycarbonyl-2-phenyl-3-thiazolidinyl)-2-oxoethyl]ureido}phenoxyacetic acid are thus obtained in the form of an amorphous solid ([α]D20 =+63.7°±1.2° (C=0.96%; 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.: 4.5 (bs, 2H, OCH2CO2); 6.5 (ddd, 1H, N--C6H4 --C in position 4); 6.9 (d, 1H aromatic); 7.1 to 7.7 (m, 7H, aromatic). Infrared spectrum (KBr), characteristic bands in cm-1 : 3380, 2975, 2930, 2630, 2550, 1735, 1640, 1600, 1555, 1490, 1370, 1240, 1150, 770, 730, 695].

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-159dcb2f88894f1cb289c7e2ddda9da3
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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