Ammonia → HCID 67491225, compound

HRID 1917365Notes

Reaction equation

HRID 1917365 reaction equation
C(OC([N:11]1[CH2:18][C@@H:17]2[C@@:13]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([CH:14]=[CH:15][CH2:16]2)[CH2:12]1)=O)C1C=CC=CC=1.[Na].N.[OH-].[Na+]>O1CCCC1.[Cl-].[NH4+]>[C:23]([O:22][C:20]([NH:19][C@@:13]12[CH:14]=[CH:15][CH2:16][C@@H:17]1[CH2:18][NH:11][CH2:12]2)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 67490772HCID 67490772, compound

Product 1

HCID 67491225HCID 67491225, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

[(1S,5R)-1-tert-Butoxycarbonylamino-3-azabicyclo[3.3.0]oct-7-en-3-yl]carboxylic acid benzyl ester (85.0 mg, 0.24 mmol) was dissolved in tetrahydrofuran (20 mL). After bubbling with liquid ammonia (20 mL) at −78° C., sodium (17.1 mg, 0.71 mmol) was added, and the mixture was stirred for one hour. A saturated ammonium chloride solution (6 drops) were added, and then ammonia was vaporized in an ice water bath. A 1N sodium hydroxide solution was added, followed by extraction with chloroform twice. The organic layers were combined, dried over anhydrous sodium sulfate, and filtered. Then, the filtrate was concentrated under reduced pressure to give 52.9 mg of the title compound as a colorless solid.

Workup

  1. customAfter bubbling with liquid ammonia (20 mL) at −78° C.
  2. extractionfollowed by extraction with chloroform twice
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThen, the filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-06a8bd5f28444e70921f89cf26c8d080
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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