Water → HCID 59383039, compound

HRID 1254397Notes

Reaction equation

HRID 1254397 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C@@:14]([C:22]2[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=2)[C:25](O)=[O:26])([OH:21])[CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[NH4+:37].[OH-].O>C(Cl)Cl.CN(C=O)C>[C:25]([C:24]1[CH:23]=[C:22]([C@:14]([C@@H:10]2[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]2)([OH:21])[CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])[CH:30]=[CH:29][CH:28]=1)(=[O:26])[NH2:37]

Participants

7

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 59383053HCID 59383053, compound

Product 1

HCID 59383039HCID 59383039, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-((S)-1-((R)-1-(tert-butoxycarbonyl)piperidin-3-yl)-1-hydroxy-5-methoxypentyl)benzoic acid (51.0 mg, 0.12 mmol) in CH2Cl2 (2 mL) was added oxalyl chloride (17.3 mg, 0.13 mmol) followed by DMF (1 drop). The resulting mixture was stirred until gas evolution ceased (˜10 min), and completion of reaction was confirmed by LC-MS. To the reaction flask was added excess NH4OH, and reaction was stirred at rt for another 10 min. Water (5 mL) was added and organic layer was separated. The aqueous layer was extracted with CH2Cl2 (2×5 mL) and the combined organic layers were washed with brine (5 mL), dried over Na2SO4, and concentrated under vacuum to give (R)-tert-butyl 3-((S)-1-(3-carbamoylphenyl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxylate (26.2 mg, 52%). MS m/z 443 (M+Na+).

Workup

  1. custom(˜10 min), and completion of reaction
  2. additionTo the reaction flask was added excess
  3. stirringwas stirred at rt for another 10 min
  4. customorganic layer was separated
  5. extractionThe aqueous layer was extracted with CH2Cl2 (2×5 mL)
  6. washthe combined organic layers were washed with brine (5 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-965be422a14e42cd83389c2d106eeefc
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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