Ethylamine → HCID 21835834, compound

HRID 1741443Notes

Reaction equation

HRID 1741443 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[CH3:30])[CH2:5][O:6][CH2:7][CH2:8][NH:9][C:10](=[O:26])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]=[N+]=[N-])=[C:14]([O:24][CH3:25])[CH:13]=1.C(N)C.[BH4-].[Na+]>C(O)(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(S)CCS>[CH3:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[CH3:30])[CH2:5][O:6][CH2:7][CH2:8][NH:9][C:10](=[O:26])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][NH2:21])=[C:14]([O:24][CH3:25])[CH:13]=1

Participants

7

Reactant 3

HCID 6341EthylamineHCID 4311764Sodium borohydrideHCID 21835821HCID 21835821, compound

Product 1

HCID 21835834HCID 21835834, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 80131,3-PropanedithiolCatalystHCID 311Citric AcidSolventHCID 3776IsopropanolSolvent2×

Procedure

2.70 g (6.54 mmol) of N-{2-(3,4-dimethylbenzyloxy)-ethyl}-4-(2-azidoethoxy)-3-methoxyphenylacetamide obtained in step 1 was dissolved in 100 ml of isopropanol and 1.82 ml (13.31 mmol) of ethylamine was added thereto with stirring. 66 ml(6.54 1nmol) of 1,3-propanedithiol was dissolved in isopropanol to a concentration of 0.1M, to which the solution prepared above and 2.48 g (6.54 mmol) of NaBH4 were slowly added. The resulting mixture was stirred at an ambient temperature for 1 hour and then the solvent was removed under a reduced pressure to produce a residue, which was dissolved in 10% citric acid. The resulting solution was washed with 30 ml of a mixture of ether: hexane (1:1) three times. The pH of the aqueous layer was adjusted to 12 with sodium hydroxide solution, and a saturated sodium chloride solution was added thereto. The resultant was extracted with 30 ml of dichloromethane 3 times and the organic layer was dried and concentrated under a reduced pressure to produce a solid, which was recrystallized from ethyl acetate/hexane to obtain 1.82 g (yield 72%) of the title compound as a white solid.

Workup

  1. additionwere slowly added
  2. stirringThe resulting mixture was stirred at an ambient temperature for 1 hour
  3. customthe solvent was removed under a reduced pressure
  4. customto produce a residue, which
  5. washThe resulting solution was washed with 30 ml of a mixture of ether: hexane (1:1) three times
  6. additiona saturated sodium chloride solution was added
  7. extractionThe resultant was extracted with 30 ml of dichloromethane 3 times
  8. customthe organic layer was dried
  9. concentrationconcentrated under a reduced pressure
  10. customto produce a solid, which
  11. customwas recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ed21de57dbfd48519f7d58f51b6d4d45
Source dataset
uspto-grants-1999_10
Patent number
US05973201

Reaction notes

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