Lithium Hydroxide → HCID 57965700, compound

HRID 1673256Notes

Reaction equation

HRID 1673256 reaction equation
C[O:2][C:3](=[O:36])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[CH:18][C:19](=[O:35])[NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:13][CH:12]=1)[N:5]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6]1.[Li+].[OH-]>CO>[C:31]([O:30][C:28]([NH:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[NH:20][C:19](/[CH:18]=[CH:17]/[C:14]1[CH:13]=[CH:12][C:11]([CH:4]([N:5]2[CH2:9][CH2:8][C@H:7]([OH:10])[CH2:6]2)[C:3]([OH:36])=[O:2])=[CH:16][CH:15]=1)=[O:35])=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66911390HCID 66911390, compound

Product 1

HCID 57965700HCID 57965700, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of {4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-(3-hydroxy-pyrrolidin-1-yl)-acetic acid methyl ester (1.23 g, 2.5 mmol) in MeOH (30 mL) was added aqueous LiOH (1 N, 10 mL), 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 0.85 g (81%) of a yellow solid product. MS: calc'd 482 (MH+), exp 482 (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-4a159d32099d4217b75563a9d41e7ea2
Source dataset
uspto-grants-2011_08
Patent number
US07999000B2

Reaction notes

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