Lithium Hydroxide → HCID 22988682, compound

HRID 987302Notes

Reaction equation

HRID 987302 reaction equation
C[O:2][C:3](=[O:34])[CH:4]([O:29][CH2:30][CH2:31][O:32][CH3:33])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1.[OH-].[Li+]>O1CCCC1.O.O>[C:25]([O:24][C:22]([NH:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH2:13][O:12][C:9]2[CH:8]=[CH:7][C:6]([CH2:5][CH:4]([O:29][CH2:30][CH2:31][O:32][CH3:33])[C:3]([OH:34])=[O:2])=[CH:11][CH:10]=2)=[CH:20][CH:19]=1)=[O:23])([CH3:26])([CH3:27])[CH3:28]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57190689HCID 57190689, compound

Product 1

HCID 22988682HCID 22988682, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

3-[4-(2-{4-tert-Butoxycarbonylaminophenyl}ethoxy)phenyl]-2-(2-methoxyethoxy)propanoic acid methyl ester (described in Example 58) (0.26 g; 0.55 mmole) was dissolved in tetrahydrofuran:water (1:3, 4 ml). Lithium hydroxide (16.0 mg; 0.66 mmole) dissolved in a small amount of water was added. The reaction mixture was stirred two hours at room temperature and then evaporated. The residue was redissolved in diethyl ether and hydrochloric acid (2M) and extracted. The organic phase was dried with magnesium sulfate and evaporated to give 0.235 g (92% yield) of 3-[4-(2-{4-tert-butoxycarbonylaminophenyl}ethoxy)phenyl]-2-(2-methoxyethoxy)propanoic acid.

Workup

  1. additionwas added
  2. customevaporated
  3. dissolutionThe residue was redissolved in diethyl ether
  4. extractionhydrochloric acid (2M) and extracted
  5. dry with materialThe organic phase was dried with magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-4ee92fc12ba142bc9477783251301e47
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

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