Acetic Acid → HCID 53941456, compound

HRID 329214Notes

Reaction equation

HRID 329214 reaction equation
[C:1]12([S:11][CH2:12][CH2:13][NH:14][C@H:15]([C:17]([OH:19])=[O:18])[CH3:16])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(O)(=O)C.[N:24]([O-])=[O:25].[Na+]>O>[C:1]12([S:11][CH2:12][CH2:13][N:14]([N:24]=[O:25])[C@H:15]([C:17]([OH:19])=[O:18])[CH3:16])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 22797218HCID 22797218, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 53941456HCID 53941456, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 22.7 parts of N-[2-(1- adamantylthio)ethyl]alanine in 216 parts of acetic acid is cooled to 15°, then treated with a solution of 6.2 parts of sodium nitrite in 20 parts of water, added dropwise over a 15 minute period. Stirring is continued at low temperature for an additional 15 minutes, then at room temperature for another 15 minutes. The resultant clear yellow solution is added to 1000 parts of ice-water and stirring is continued. The resultant mixture is extracted with methylene chloride. The organic phase is separated, washed with water, dried over anhydrous sodium sulfate and evaporated to dryness to yield, as a gumlike material, N-[2-(1-adamantylthio)ethyl]-N-nitrosoalanine.

Workup

  1. additionadded dropwise over a 15 minute period
  2. waitat room temperature for another 15 minutes
  3. stirringstirring
  4. extractionThe resultant mixture is extracted with methylene chloride
  5. customThe organic phase is separated
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-6b8ffa7036c04c0392aa2b0f69d9629c
Source dataset
uspto-grants-1977_04
Patent number
US04020079

Reaction notes

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