1-bromohex-5-en-2-one → HCID 44550118, compound

HRID 1924376Notes

Reaction equation

HRID 1924376 reaction equation
[NH2:1][C:2]([NH:4][C@H:5]([C:9]([N:11]1[CH2:19][C@H:18]([O:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([CH:31]=[CH2:32])[CH:29]=3)[CH:24]=[CH:23][N:22]=2)[CH2:17][C@H:12]1[C:13]([O:15][CH3:16])=[O:14])=[O:10])[CH:6]([CH3:8])[CH3:7])=[S:3].Br[CH2:34][C:35](=O)[CH2:36][CH2:37][CH:38]=[CH2:39]>O1CCOCC1>[CH2:36]([C:35]1[N:1]=[C:2]([NH:4][C@H:5]([C:9]([N:11]2[CH2:19][C@H:18]([O:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[C:28]([CH:31]=[CH2:32])[CH:29]=4)[CH:24]=[CH:23][N:22]=3)[CH2:17][C@H:12]2[C:13]([O:15][CH3:16])=[O:14])=[O:10])[CH:6]([CH3:8])[CH3:7])[S:3][CH:34]=1)[CH2:37][CH:38]=[CH2:39]

Participants

4

Reactant 2

HCID 106788641-bromohex-5-en-2-oneHCID 44549611HCID 44549611, compound

Product 1

HCID 44550118HCID 44550118, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of thiourea from Step 3 and Intermediate 3 (1.5 eq) in dioxane was stirred at 65° C. for 1 h. The volatiles were then removed under reduced pressure and the residue was purified by SiO2 gel chromatography (DCM/MeOH=98/2) to give the title compound as a pale brown oil. MS (ES+) C29H34N4O4S requires: 534. Found: 535 (M+H+).

Workup

  1. customThe volatiles were then removed under reduced pressure
  2. customthe residue was purified by SiO2 gel chromatography (DCM/MeOH=98/2)

Sources & evidence

ORD record
ord-301aad0d5e32437a9c100c48a2c2c022
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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