Hydrochloric Acid → HCID 68154436, compound

HRID 1615734Notes

Reaction equation

HRID 1615734 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([C@@H:10]([NH2:13])[CH2:11][NH2:12])[CH:6]=[C:7]([F:9])[CH:8]=1.[OH-:14].[Na+].[O:16]1[CH2:22][C:21](=O)[CH2:20][O:19][CH2:18][CH2:17]1.[CH:24](Cl)(Cl)Cl.Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[F:2][C:3]1[CH:4]=[C:5]([C@H:10]2[NH:13][C:24](=[O:14])[C:21]3([CH2:22][O:16][CH2:17][CH2:18][O:19][CH2:20]3)[NH:12][CH2:11]2)[CH:6]=[C:7]([F:9])[CH:8]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 468563761,4-Dioxepan-6-oneHCID 66516887HCID 66516887, compound

Product 1

HCID 68154436HCID 68154436, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

3.13 g (15.0 mmol) (R)-1-(3,5-difluorophenyl)ethan-1,2-diamine-hydrochloride were placed with 0.17 g (0.73 mmol) benzyltriethylammonium chloride in 30 ml dichloromethane and cooled with ice/acetone. Then 5.21 ml (102.2 mmol) of a 50% sodium hydroxide solution were added. At 0° C. to 2° C., 1.70 g (14.6 mmol) [1,4]dioxepan-6-one together with 1.83 ml (22.7 mmol) chloroform and 20 ml dichloromethane were added dropwise within 1.5 h. The mixture was left overnight to warm up to RT. Then it was cooled to 0° C. and the reaction mixture was adjusted to pH1 with a 6N aqueous hydrochloric acid solution. The phases were separated. The aqueous phase was made alkaline with a 4N sodium hydroxide solution and extracted with ethyl acetate. The combined organic phases were dried and evaporated to dryness by rotary evaporation. Purification was carried out by flash chromatography.

Workup

  1. temperatureThen it was cooled to 0° C.
  2. customThe phases were separated
  3. extractionextracted with ethyl acetate
  4. customThe combined organic phases were dried
  5. customevaporated to dryness by rotary evaporation
  6. customPurification

Sources & evidence

ORD record
ord-6aa5331acc2443e0b7f92e706b4c95d8
Source dataset
uspto-grants-2014_07
Patent number
US08765763B2

Reaction notes

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