Sodium Hydroxide → HCID 15605152, compound

HRID 732714Notes

Reaction equation

HRID 732714 reaction equation
[C:1]1([C@H:11]([NH:13][CH2:14][C@@H:15]2[C@@H:19]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[CH2:18][N:17]([C:30](=[O:45])[CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:37]CC3C=CC=CC=3)=[O:36])[CH2:16]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CO.C1COCC1>[C:1]1([C@H:11]([NH:13][CH2:14][C@@H:15]2[C@@H:19]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:27])[F:28])[CH:21]=3)[CH2:18][N:17]([C:30](=[O:45])[CH2:31][CH2:32][CH2:33][CH2:34][C:35]([OH:37])=[O:36])[CH2:16]2)[CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68912188HCID 68912188, compound

Product 1

HCID 15605152HCID 15605152, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 310 mg portion of benzyl 6-{(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-[3-(trifluoromethyl)phenyl]pyrrolidin-1-yl}-6-oxohexanoate was dissolved in 2 ml of methanol and 2 ml of THF, mixed with 2 ml of 1 M sodium hydroxide aqueous solution at room temperature and stirred for 16 hours. The reaction solution was washed with diethyl ether, 1 M hydrochloric acid was added to the water layer until its pH became 2.0, and then this was extracted with chloroform. After washing this with saturated brine, the organic layer was dried with anhydrous sodium sulfate and concentrated under a reduced pressure. By purifying the thus obtained residue by a silica gel column chromatography (chloroform-methanol), 6-{(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-[3-(trifluoromethyl)phenyl]pyrrolidin-1-yl}-6-oxohexanoic acid was obtained. The thus obtained compound was dissolved in 2 ml of 4 M hydrogen chloride/1,4-dioxane solution and then concentrated under a reduced pressure. THF and diethyl ether were added to the residue, the thus obtained precipitate was collected by filtration, and the filtered product was dried under a reduced pressure to obtain 200 mg of 6-{(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-[3-(trifluoromethyl)phenyl]pyrrolidin-1-yl}-6-oxohexanoic acid hydrochloride as a colorless solid.

Workup

  1. washThe reaction solution was washed with diethyl ether, 1 M hydrochloric acid
  2. additionwas added to the water layer until its pH
  3. extractionthis was extracted with chloroform
  4. washAfter washing this with saturated brine
  5. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customBy purifying the thus obtained residue by a silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-d1277b8a78174209939b75f4208f4d11
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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