Triethylamine → HCID 57868852, compound

HRID 1966133Notes

Reaction equation

HRID 1966133 reaction equation
[CH:1]1([S:4]([N:7]2[CH2:10][CH:9]([OH:11])[CH2:8]2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22].C(=O)(O)[O-].[Na+]>O1CCCC1.CN(C)C1C=CN=CC=1>[CH:1]1([S:4]([N:7]2[CH2:8][CH:9]([O:11][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH2:10]2)(=[O:5])=[O:6])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 13819ChlorotriethylsilaneHCID 516892Sodium BicarbonateHCID 57868875HCID 57868875, compound

Product 1

HCID 57868852HCID 57868852, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(cyclopropylsulfonyl)azetidin-3-ol (1.04 g, 5.87 mmol) and triethylamine (3.11 mL, 22.3 mmol) in tetrahydrofuran (20 mL) was added 4-dimethylaminopyridine (0.090 g, 0.73 mmol) followed by chlorotriethylsilane (1.00 M in THF, 8.0 mL, 8.0 mmol). The reaction was stirred at room temperature for 16 hours. To the reaction was added saturated sodium bicarbonate solution and the product was extracted with a 1:1 mix of ethyl acetate:hexanes three times. The combined organic extracts were washed with dilute HCl and brine, then dried over sodium sulfate, decanted and concentrated. Flash column chromatography, eluting with a gradient of 0-50% ethyl acetate in hexanes afforded desired product (1.0 g, 58%).

Workup

  1. extractionthe product was extracted with a 1:1
  2. additionmix of ethyl acetate
  3. washThe combined organic extracts were washed with dilute HCl and brine
  4. dry with materialdried over sodium sulfate
  5. customdecanted
  6. concentrationconcentrated
  7. washFlash column chromatography, eluting with a gradient of 0-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-e7a9c3ffd6ce4e459839297259943d9f
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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