Methanol → HCID 68914504, compound

HRID 732672Notes

Reaction equation

HRID 732672 reaction equation
C(OC([N:8]([CH2:21][C@@H:22]1[C@@H:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:25][N:24]([C:33](=[O:41])[CH2:34][CH2:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39])[CH2:23]1)[C@@H:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:10])=O)(C)(C)C.CO.[ClH:44].O1CCOCC1>>[ClH:44].[C:11]1([C@H:9]([NH:8][CH2:21][C@@H:22]2[C@@H:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:25][N:24]([C:33](=[O:41])[CH2:34][CH2:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39])[CH2:23]2)[CH3:10])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 204431481,4-Dioxane hydrochlorideHCID 68912635HCID 68912635, compound

Product 1

HCID 68914504HCID 68914504, compound

Procedure

A 237 mg portion of 6-[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]-6-oxohexanoic acid was dissolved in 2.0 ml of 4 M hydrogen chloride/1,4-dioxane solution and 2.0 ml of methanol at room temperature and stirred for 62Hours. The reaction solution was concentrated under a reduced pressure, and the thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol) and then dissolved in 2.0 ml of ethyl acetate, mixed with 1.0 ml of 4 M hydrogen chloride/ethyl acetate solution and concentrated under a reduced pressure. The residue was dissolved in ethanol and mixed with ethyl acetate, and the thus obtained precipitate was collected by filtration and dried under a reduced pressure to obtain 40 mg of 6-[(3S,4S)-3-({[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]-6-oxohexanoic acid hydrochloride as a colorless solid.

Workup

  1. concentrationThe reaction solution was concentrated under a reduced pressure
  2. customthe thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol)
  3. dissolutiondissolved in 2.0 ml of ethyl acetate
  4. additionmixed with 1.0 ml of 4 M hydrogen chloride/ethyl acetate solution
  5. concentrationconcentrated under a reduced pressure
  6. dissolutionThe residue was dissolved in ethanol
  7. additionmixed with ethyl acetate
  8. filtrationthe thus obtained precipitate was collected by filtration
  9. customdried under a reduced pressure

Sources & evidence

ORD record
ord-15eaf18427464290aec2b25ab0d1b307
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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