Lithium Hydroxide → HCID 69221122, compound

HRID 130377Notes

Reaction equation

HRID 130377 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]2[CH:13]([CH2:33][O:34]C(=O)C)[CH:14]([NH:16][C:17](=[O:32])[CH2:18][NH:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[CH2:15][CH:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]2[CH:13]([CH2:33][OH:34])[CH:14]([NH:16][C:17](=[O:32])[CH2:18][NH:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[CH2:15][CH:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69224759HCID 69224759, compound

Product 1

HCID 69221122HCID 69221122, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-acetoxymethyl-5-[2-(3-trifluoromethylbenzoylamino)acetylamino]octahydrocyclopenta[c]-pyrrole-2-carboxylic acid tert-butyl ester in tetrahydrofuran is treated with aqueous lithium hydroxide and the mixture is stirred at room temperature until the reaction is complete. The reaction mixture is concentrated under vacuum yielding an aqueous residue. The aqueous residue is extracted with ethyl acetate, and the organic phases are dried over sodium sulfate and concentrated under vacuum yielding a residue. The residue is purified by flash column chromatography providing the title product.

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. customyielding an aqueous residue
  3. extractionThe aqueous residue is extracted with ethyl acetate
  4. dry with materialthe organic phases are dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customyielding a residue
  7. customThe residue is purified by flash column chromatography

Sources & evidence

ORD record
ord-e09a25b04bcb40b39e6c4b607d19b6b7
Source dataset
uspto-grants-2008_06
Patent number
US07381738B2

Reaction notes

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