Lithium Hydroxide → HCID 54332753, compound

HRID 975969Notes

Reaction equation

HRID 975969 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]([CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])[CH:27]=[CH:28][CH:29]=1)=[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]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH:27]=[CH:28][CH:29]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 53965743HCID 53965743, compound

Product 1

HCID 54332753HCID 54332753, compoundYield 10.5%

Procedure

The operation is carried out in a fashion similar to that described in Example 39, but starting from 2.5 g of ethyl (2R,4R)-3-{3-{3-[2-(4-tert-butoxycarbonyl-2-phenyl-3-thiazolidinyl)-2-oxoethyl]ureido}phenyl}propionate and 0.2 g of lithium hydroxide. The crude product is purified by chromatography on silica [eluent: ethyl acetate/methanol (90/10 by volume)]. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure at 40° C. 0.25 g of (2R,4R)-3-{3-{3-[2-(4-tert-butoxycarbonyl-2-phenyl-3-thiazolidinyl)-2-oxoethyl]ureido}phenyl}propionic acid is thus obtained in the form of an amorphous beige solid ([α]D20 =+58.4°±1.6° (C=0.61%; CHCl3)) [proton NMR (200 MHz, DMSO D6, δ in ppm), 2 rotamers at room temperature, characteristic chemical shifts at 25° C.: 1.5 (bs, 9H, (CH3)3); 2.5 (bt, 2H, CH2); 2.8 (bt, 2H, CH2); 6.8 (bd, 1H, N--C6H4 --C in position 4); 7.1 to 7.5 (m, 7H, aromatic); 7.7 (bd, 2H, aromatic). Infrared spectrum (KBr), characteristic bands in cm-1 : 3380, 2975, 2930, 2620, 1730, 1645, 1610, 1590, 1555, 1490, 1370, 1235, 1150, 785, 730, 695].

Workup

  1. customThe crude product is purified by chromatography on silica [eluent: ethyl 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-6d45494d31694154be0504eb63aa8f1f
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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