Water → HCID 53878528, compound

HRID 1645931Notes

Reaction equation

HRID 1645931 reaction equation
[H-].[Na+].[NH2:3][CH2:4][CH2:5][SH:6].Cl[CH2:8][CH:9]=[C:10]([CH3:52])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:51])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:50])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:49])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:48])[CH2:27][CH2:28][CH:29]=[C:30]([CH3:47])[CH2:31][CH2:32][CH:33]=[C:34]([CH3:46])[CH2:35][CH2:36][CH:37]=[C:38]([CH3:45])[CH2:39][CH2:40][CH:41]=[C:42]([CH3:44])[CH3:43].O>O1CCCC1.C1OCCOCCOCCOCCOCCOC1>[CH3:52][C:10]([CH2:11][CH2:12][CH:13]=[C:14]([CH3:51])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:50])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:49])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:48])[CH2:27][CH2:28][CH:29]=[C:30]([CH3:47])[CH2:31][CH2:32][CH:33]=[C:34]([CH3:46])[CH2:35][CH2:36][CH:37]=[C:38]([CH3:45])[CH2:39][CH2:40][CH:41]=[C:42]([CH3:44])[CH3:43])=[CH:9][CH2:8][S:6][CH2:5][CH2:4][NH2:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6058CysteamineHCID 24758Sodium hydrideHCID 54384730HCID 54384730, compound

Product 1

HCID 53878528HCID 53878528, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Under an atmosphere of argon, sodium hydride (1.43 g, 35.8 mmol, 60% dispersion in mineral oil) was added to a solution of 2-aminoethanethiol (2.76 g, 35.8 mmol) in 90 ml of tetrahydrofuran. The mixture was heated at reflux temperature for 15 minutes and cooled in an ice bath. To the reaction mixture, 18-crown-6 (20 mg, 0.08 mmol) was added and then a solution of 1-chloro-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaene [23.2 g, 35.7 mmol, prepared as described in Item a) given above] in 90 ml of tetrahydrofuran was added in dropwise for 10 minutes. The reaction mixture was heated at reflux temperature for 4 hours and then cooled. After addition of water (1 ml), the solvent was evaporated in vacuo to dryness. The remaining residue was partitioned between water and n-hexane. The aqueous layer was extracted with n-hexane to combine the n-hexane layers. The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to dryness. The remaining residue was chromatographed on silica gel, eluting with CH2Cl2 /MeOH (50:1-20:1) to afford 15.1 g (61.3%) of the desired compound, as a pale brown oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 15 minutes
  3. temperaturecooled in an ice bath
  4. additionwas added in dropwise for 10 minutes
  5. temperatureThe reaction mixture was heated
  6. temperatureat reflux temperature for 4 hours
  7. temperaturecooled
  8. customthe solvent was evaporated in vacuo to dryness
  9. customThe remaining residue was partitioned between water and n-hexane
  10. extractionThe aqueous layer was extracted with n-hexane
  11. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. customevaporated in vacuo to dryness
  14. customThe remaining residue was chromatographed on silica gel
  15. washeluting with CH2Cl2 /MeOH (50:1-20:1)

Sources & evidence

ORD record
ord-d7421b3bc67849ac869dc65473f0f215
Source dataset
uspto-grants-1993_01
Patent number
US05177102

Reaction notes

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