Sodium Carbonate → HCID 59627251, compound

HRID 1523240Notes

Reaction equation

HRID 1523240 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C@@:13]([NH:24][S@@](C(C)(C)C)=O)([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:14][CH:15]=[CH2:16])[CH3:9])=[CH:4][CH:3]=1.O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C@:13]([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)([NH2:24])[CH2:14][CH:15]=[CH2:16])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 68731783HCID 68731783, compound

Product 1

HCID 59627251HCID 59627251, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (R)—N—((R)-1-((S)-1-(4-bromophenyl)ethylamino)-3-(4-fluorophenyl)hex-5-en-3-yl)-2-methylpropane-2-sulfinamide (16 g, 32.2 mmol) in 4M HCl in dioxane (100 mL, 400 mmol) was stirred for 1 h at 0° C. The mixture was concentrated to give the residue, which was treated with saturated Na2CO3 solution. The resulting mixture was extracted with EtOAc, and the combined organic layers was concentrated to afford (R)—N1—((S)-1-(4-bromophenyl)ethyl)-3-(4-fluorophenyl)hex-5-ene-1,3-diamine (12 g, 100%), which was used for the next step without purification.

Workup

  1. concentrationThe mixture was concentrated
  2. customto give the residue, which
  3. extractionThe resulting mixture was extracted with EtOAc
  4. concentrationthe combined organic layers was concentrated

Sources & evidence

ORD record
ord-ff9e7efa39de4e878353c9d5b00ece4e
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

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