Hydrochloric Acid → HCID 123642409, compound

HRID 1755505Notes

Reaction equation

HRID 1755505 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[CH:18][S:17][C:16]=2[CH:20]=[CH:21][C:22]2[CH:40]=[CH:39][C:25]([N:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:24][CH:23]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Br:41]N1C(=O)CCC1=O.Cl>CN(C=O)C>[Br:41][C:18]1[S:17][C:16]([CH:20]=[CH:21][C:22]2[CH:23]=[CH:24][C:25]([N:26]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:39][CH:40]=2)=[C:15]([C:12]2[CH:13]=[CH:14][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:10][CH:11]=2)[CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67184N-bromobutanimide2×HCID 117602575HCID 117602575, compound

Product 1

HCID 123642409HCID 123642409, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a three necked flask under argon, 1.00 g (1.85 mmol, 1 eq.) of YKP70 in 20 mL of DMF are cooled to −10° C. 328 mg (1.85 mmol, 1 eq.) of N-bromosuccinimide are solubilised in 10 mL of mixture [DMF/MeOH:1/1]. This solution of NBS (protected from light) is then added drop by drop (30 min) into the reaction medium. The temperature of the medium is then left to rise to ambient temperature over 2 h. The medium is hydrolysed with a 1 mol·L−1 HCl solution and extracted with ethyl ether. The combined organic phases are washed with a saturated NaCl solution then dried on anhydrous Na2SO4. After drying on Na2SO4, filtration and evaporation of the solvent, the purification is carried out on neutral alumina column with the eluent [hexane/CHCl3: 100/1]. 742 mg of final compound YKP69 are obtained in the form of a translucent oil (yield of 64.6%).

Workup

  1. waitThe temperature of the medium is then left
  2. extractionextracted with ethyl ether
  3. washThe combined organic phases are washed with a saturated NaCl solution
  4. dry with materialthen dried on anhydrous Na2SO4
  5. customAfter drying on Na2SO4, filtration and evaporation of the solvent
  6. customthe purification

Sources & evidence

ORD record
ord-b0f0ca00165a49378528634ca6866ce4
Source dataset
uspto-grants-2015_10
Patent number
US09171676B2

Reaction notes

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