Triethylamine → HCID 178457364, compound

HRID 2417973Notes

Reaction equation

HRID 2417973 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[CH2-:6][C:7]([CH3:9])=[O:8].[CH:10]([NH:13][CH2:14][C@H:15]([OH:18])[CH2:16][OH:17])([CH3:12])[CH3:11].C(N(CC)CC)C>O1CCCC1.[Cl-].[Na+].O>[CH2-:6][C:7]([CH3:9])=[O:8].[S:1]([N:13]([CH:10]([CH3:12])[CH3:11])[CH2:14][C@H:15]([OH:18])[CH2:16][OH:17])([CH3:4])(=[O:3])=[O:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178457363HCID 178457363, compound

Product 1

HCID 178457364HCID 178457364, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

90 ml mesyl chloride was added with stirring to a previously chilled (-10°) solution of (2S)-3-isopropylamino-1,2-propanediol acetonide (188 g; 1.087 mol) and triethylamine (228 ml; 1.63 mol) in dry tetrahydrofuran at such a rate that the reaction temperature did not exceed 5°. Reaction was then stirred at 10°-15° for 30 minutes whereupon it was diluted with 1.5 L brine. The layers were separated and the aqueous layers were extracted with ether (3×500 ml). The organic layers were washed in turn with brine (2×500 ml) and then were combined, dried over sodium sulfate, and evaporated to give 264 g of (2S)-3-[N-mesyl-(1-methylethyl)amino]-1,2-propanediol acetonide as an oil.

Workup

  1. customdid not exceed 5°
  2. customReaction
  3. stirringwas then stirred at 10°-15° for 30 minutes whereupon it
  4. customThe layers were separated
  5. extractionthe aqueous layers were extracted with ether (3×500 ml)
  6. washThe organic layers were washed in turn with brine (2×500 ml)
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-e49727269b4240c6b875ee74dc43ce20
Source dataset
uspto-grants-1984_09
Patent number
US04471116

Reaction notes

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