Triethylamine → HCID 178418975, compound

HRID 711949Notes

Reaction equation

HRID 711949 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:23][S:24]([O:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:15])[CH2:4][CH2:3]1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178418329HCID 178418329, compound

Product 1

HCID 178418975HCID 178418975, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl (trans-4-hydroxycyclohexyl)carbamate (from AstaTech, 0.133 g, 0.618 mmol) and triethylamine (0.12 mL, 0.86 mmol) in methylene chloride (1 mL) was added methanesulfonyl chloride (0.057 mL, 0.74 mmol). The reaction mixture was stirred at room temperature for 2 h. After dilution with sat. aq. NaHCO3 solution, the mixture was extracted with dichloromethane. The combined organic layers were washed with brine, dried over MgSO4 and concentrated to give the desired product (0.18 g, 99%).

Workup

  1. extractionAfter dilution with sat. aq. NaHCO3 solution, the mixture was extracted with dichloromethane
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-568b1d783f78419096db8fbfdcb26f4b
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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