Triethylamine → HCID 86598964, compound

HRID 1158558Notes

Reaction equation

HRID 1158558 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[C:6]([S:25][CH2:26][CH2:27][CH2:28][OH:29])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C1COCC1>[C:6]([S:25][CH2:26][CH2:27][CH2:28][O:29][S:1]([CH3:4])(=[O:3])=[O:2])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15217100HCID 15217100, compound

Product 1

HCID 86598964HCID 86598964, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mesyl chloride (6 μl, 0.075 mmol) was added to a solution of 3-tritylsulfanyl-propan-1-ol (5 mg, 0.015 mmol) and triethyl amine (32 μl, 0.23 mmol) in THF (1 ml). After 30 minutes THF was evaporated under reduced pressure and the crude product dissolved in DCM, washed with a saturated solution of sodium hydrogencarbonate in water, a saturated solution of sodium chloride and dried with MgSO4. A yield of 10 mg was obtained after evaporation under reduced pressure (analytical HPLC: column Luna C18,00B-4251-E0: solvents: A=water/0.1% TFA and B=CH3CN/0.1% TFA; gradient 40-80% B over 10 min; flow 1.0 ml/minute; retention time 7.12 minutes detected at 214 and 254 nm). Structure verified by NMR.

Workup

  1. customAfter 30 minutes THF was evaporated under reduced pressure
  2. dissolutionthe crude product dissolved in DCM
  3. washwashed with a saturated solution of sodium hydrogencarbonate in water
  4. dry with materiala saturated solution of sodium chloride and dried with MgSO4
  5. customA yield of 10 mg was obtained
  6. customafter evaporation under reduced pressure (analytical HPLC

Sources & evidence

ORD record
ord-0854f26bfcb1457089233697b14a170f
Source dataset
uspto-grants-2010_10
Patent number
US07811551B2

Reaction notes

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