Sodium borohydride → HCID 14076215, compound

HRID 2210330Notes

Reaction equation

HRID 2210330 reaction equation
[C:1]([NH:9][C:10]1[S:11][CH:12]=[C:13]([C:15](=[O:18])[CH2:16]Br)[N:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH2:32])=[CH:26][CH:25]=1)([O:21][CH2:22][CH3:23])=[O:20].[BH4-].[Na+]>C(Cl)Cl.CO.NC(N)=O>[C:19]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][NH:32][CH2:16][CH:15]([OH:18])[C:13]2[N:14]=[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[S:11][CH:12]=2)=[CH:26][CH:25]=1)([O:21][CH2:22][CH3:23])=[O:20]

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 12945884Ethyl 4-(2-aminoethyl)benzoateHCID 14076214HCID 14076214, compound

Product 1

HCID 14076215HCID 14076215, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1176UreaSolventHCID 6344DichloromethaneSolvent2×

Procedure

9.6 g (0.03 mol) of 2-Benzoylamino-4-bromoacetyl-thiazole are dissolved in 100 ml of methylene chloride and, while stirring at room temperature, added dropwise to a solution of 11.5 g (0.06 mol) of 2-(4-carboethoxyphenyl)ethylamine in 150 ml of methylene chloride. After 1.5 hours, the mixture is cooled to 5° C., diluted with 200 ml of methanol and, for the reduction of the resulting amino-ketone, 3 g of sodium borohydride are added in small portions at 0°-5° C. After 3 hours the solution is evaporated to dryness, ice/water is added, and hydrochloric acid is used to acidify. After 10 minutes the mixture is made alkaline with sodium bicarbonate solution and extracted with methylene chloride. The extract is dried over sodium sulphate, concentrated and purified on a silica gel column using chloroform/methanol =9:1, with the addition of 2% ammonia-saturated ethanol, as eluant. The resulting product is induced to crystallise with petroleum ether.

Workup

  1. temperaturethe mixture is cooled to 5° C.
  2. additionare added in small portions at 0°-5° C
  3. customAfter 3 hours the solution is evaporated to dryness, ice/water
  4. additionis added
  5. waitAfter 10 minutes the mixture is made
  6. extractionalkaline with sodium bicarbonate solution and extracted with methylene chloride
  7. dry with materialThe extract is dried over sodium sulphate
  8. concentrationconcentrated
  9. custompurified on a silica gel column
  10. additionwith the addition of 2% ammonia-saturated ethanol
  11. customto crystallise with petroleum ether

Sources & evidence

ORD record
ord-536ddc360f04463ba261fcf1827562fc
Source dataset
uspto-grants-1995_10
Patent number
US05457205

Reaction notes

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