Lithium hydroxide, monohydrate → (E)-2-{4-[2-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid

HRID 220172Notes

Reaction equation

HRID 220172 reaction equation
C([O:3][C:4](=[O:41])[CH:5]([C:16]1[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24](=[O:40])[NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])=[CH:18][CH:17]=1)[CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])C.O[Li].O>CO.O>[C:36]([O:35][C:33]([NH:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[NH:25][C:24](/[CH:23]=[CH:22]/[C:19]1[CH:18]=[CH:17][C:16]([CH:5]([CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[C:4]([OH:41])=[O:3])=[CH:21][CH:20]=1)=[O:40])=[O:34])([CH3:38])([CH3:37])[CH3:39]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59238281(E)-2-{4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester

Product 1

HCID 59238283(E)-2-{4-[2-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-4-(tert-butyl-dimethyl-silanyloxy)-butyric acidYield 80%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of (E)-2-{4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-4-(tert-butyl-dimethyl-silanyloxy)-butyric acid ethyl ester (2.63 g, 4.52 mmol) in MeOH/H2O (30 mL/10 mL) was added LiOH.H2O (556 mg, 13.56 mmol). This mixture was stirred for about 5 h at room temperature, and then evaporated to remove most of the MeOH. The aqueous layer was acidified with concentrated HCl to pH 5-6. The acidified aqueous layer was extracted with ethyl acetate (3×30 mL). The combined organic layer was washed with brine, dried with Na2SO4, filtered, and evaporated to obtain 2.0 g (80%) of a yellow solid product. MS: calc'd 555 (MH+), exp 555 (MH+).

Workup

  1. customevaporated
  2. customto remove most of the MeOH
  3. extractionThe acidified aqueous layer was extracted with ethyl acetate (3×30 mL)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a74f06dc85e34c5ba424957f92fee107
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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