Lithium Hydroxide → HCID 57965704, compound

HRID 1673259Notes

Reaction equation

HRID 1673259 reaction equation
C[O:2][C:3](=[O:40])[CH:4]([C:15]1[CH:20]=[CH:19][C:18]([CH:21]=[CH:22][C:23](=[O:39])[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:17][CH:16]=1)[N:5]1[CH2:9][CH2:8][CH:7]([N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[CH2:6]1.[Li+].[OH-]>CO>[C:35]([O:34][C:32]([NH:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[NH:24][C:23](/[CH:22]=[CH:21]/[C:18]1[CH:17]=[CH:16][C:15]([CH:4]([N:5]2[CH2:9][CH2:8][CH:7]([N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[CH2:6]2)[C:3]([OH:40])=[O:2])=[CH:20][CH:19]=1)=[O:39])=[O:33])([CH3:36])([CH3:38])[CH3:37]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66911490HCID 66911490, compound

Product 1

HCID 57965704HCID 57965704, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of {4-[2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-vinyl]-phenyl}-(3-diethylamino-pyrrolidin-1-yl)-acetic acid methyl ester (2.06 g, 3.75 mmol) in MeOH (30 mL) was added aqueous LiOH (1 N, 15 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 1.40 g (70%) of yellow solid product. MS: calc'd 537 (MH+), exp 537 (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-98dfa86f71134e478117014951a42610
Source dataset
uspto-grants-2011_08
Patent number
US07999000B2

Reaction notes

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