Triethylamine → HCID 178418975, compound

HRID 1257731Notes

Reaction equation

HRID 1257731 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:10][C:11](=[O:20])[NH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][CH2:14]1)([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:6]([O:10][C:11]([NH:12][C@H:13]1[CH2:14][CH2:15][C@H:16]([O:19][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:17][CH2:18]1)=[O:20])([CH3:9])([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 178418329HCID 178418329, compound

Product 1

HCID 178418975HCID 178418975, compoundYield 106.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (1.37 g, 929 μL, 12 mmol) was added dropwise to a stirred suspension of trans (4-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester (2.15 g, 10.0 mmol) in DCM (25 mL) and triethylamine (1.42 g, 1.95 mL, 14.0 mmol). After 2.5 hours saturated aqueous sodium hydrogen carbonate solution (25 mL) was added and the phases were separated. The aqueous phase was extracted with DCM (2×20 mL). The combined organic extracts were washed with brine (50 mL), dried over sodium sulfate and concentrated under vacuum to afford 3.13 g (100%) of trans methanesulfonic acid 4-tert-butoxycarbonylamino-cyclohexyl ester an off white solid. 1H NMR (400 MHz, CDCl3): δ 4.66-4.56 (m, 1H), 4.37 (br s, 1H), 3.46 (br s, 1H), 3.00 (s, 3H), 2.18-2.02 (m, 4H), 1.74-1.61 (m, 2H), 1.43 (s, 9H), 1.31-1.19 (m, 2H).

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with DCM (2×20 mL)
  3. washThe combined organic extracts were washed with brine (50 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c177b007434c417589078bd673c0f9ce
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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