Tert-Butylamine → HCID 13974077, compound

HRID 2292205Notes

Reaction equation

HRID 2292205 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]=[C:10]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=2)[CH:13]([CH2:26][OH:27])[CH2:12][N:11]1[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=1.[CH2:39]([CH:41]1[O:43][CH2:42]1)Br.[C:44]([NH2:48])([CH3:47])([CH3:46])[CH3:45]>CO>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[N:9]=[C:10]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=2)[CH:13]([CH2:26][O:27][CH2:39][CH:41]([OH:43])[CH2:42][NH:48][C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:12][N:11]1[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[CH:30]=1

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 18430EpibromohydrinHCID 13974076HCID 13974076, compound

Product 1

HCID 13974077HCID 13974077, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

0.13 g of Na were dissolved in 20 ml of methanol. After dissolution, 2.8 g of (9) (0.5 mol) in 10 ml of methanol were added. The mixture was refluxed for one hour. Then the solvent was evaporated. The residue was dissolved in 40 ml of DMF and 0.48 ml (5.6 mmol) of epibromohydrin were added. The mixture was stirred for 18 hours at room temperature, after which time the DMF was evaporated. The crude mixture was dissolved in 30 ml of ethanol and 1.1 g (15 mmol) of tert-butylamine were added. After evaporation of the solvent and EtOAc/water extraction, the organic layer was dried over MgSO4 and filtered. Concentration gave 3.2 g of crude product which was separated over a silica gel column using EtOAc/MeOH/ET3N: (8:1:1) as solvent. After purification, 2.1 g of (10) were obtained (yield 61%).

Workup

  1. additionwere added
  2. temperatureThe mixture was refluxed for one hour
  3. customThen the solvent was evaporated
  4. dissolutionThe residue was dissolved in 40 ml of DMF
  5. customafter which time the DMF was evaporated
  6. dissolutionThe crude mixture was dissolved in 30 ml of ethanol
  7. customAfter evaporation of the solvent and EtOAc/water extraction
  8. dry with materialthe organic layer was dried over MgSO4
  9. filtrationfiltered
  10. concentrationConcentration
  11. customgave 3.2 g of crude product which
  12. customwas separated over a silica gel column
  13. customAfter purification

Sources & evidence

ORD record
ord-0cd9eecd6f0d48c49661c670e0cb7f5a
Source dataset
uspto-grants-1989_01
Patent number
US04801617

Reaction notes

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