Pyridine → HCID 178453973, compound

HRID 711971Notes

Reaction equation

HRID 711971 reaction equation
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:5][CH2:4]1.N1C=CC=CC=1.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH3:23][S:24]([O:1][CH2:2][C@H:3]1[CH2:4][CH2:5][C@H:6]([NH:9][C:10]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:16])[CH2:7][CH2:8]1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 178453956HCID 178453956, compound

Product 1

HCID 178453973HCID 178453973, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of tert-butyl [trans-4-(hydroxymethyl)cyclohexyl]carbamate (from Albany Molecular, 1.5 g, 6.5 mmol) in methylene chloride (20 mL) was treated with pyridine (2.14 mL, 26.5 mmol). The mixture was cooled to 0° C. and methanesulfonyl chloride (1.01 mL, 13.1 mmol) was added dropwise over 5 min. The reaction was stirred at room temperature for 5 h. The resulting mixture was then concentrated and partitioned between EtOAc and water. The organic phases were concentrated and purified on silica gel (eluting with 50% EtOAc in hexanes) to give the desired product (1.48 g, 74%). LCMS calculated for C13H25NO5SNa (M+Na)+: m/z=330.2. Found: 330.0.

Workup

  1. concentrationThe resulting mixture was then concentrated
  2. custompartitioned between EtOAc and water
  3. concentrationThe organic phases were concentrated
  4. custompurified on silica gel (eluting with 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-043e2f3049b44d93811a0135904fd84c
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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