Triethylamine → Tert-butyl 4-{3-cyano-2-[(methylsulfonyl)oxy]propyl}-1,4-diazepane-1-carboxylate

HRID 1772815Notes

Reaction equation

HRID 1772815 reaction equation
[C:1]([CH2:3][CH:4]([OH:20])[CH2:5][N:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:7]1)#[N:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl.O>[C:1]([CH2:3][CH:4]([O:20][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:5][N:6]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:8][CH2:7]1)#[N:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58180980HCID 58180980, compound

Product 1

HCID 58181008Tert-butyl 4-{3-cyano-2-[(methylsulfonyl)oxy]propyl}-1,4-diazepane-1-carboxylateYield 100.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl 4-(3-cyano-2-hydroxypropyl)-1,4-diazepane-1-carboxylate (3.2 g, 11 mmol) and triethylamine (3.1 mL, 22 mmol) in DCM (60 mL) was cooled to 0° C. and treated with methanesulfonyl chloride (1.2 mL, 16 mmol). After stirring at 0° C. for 1 hour, the reaction solution was diluted with water and DCM. The organic layer was washed with water twice, dried over MgSO4, filtered, and concentrated to give the desired product as oil (4 g, 98%). The crude product was used immediately in the next step. LCMS calculated for C15H28N3O5S(M+H)+: m/z=362.1.

Workup

  1. washThe organic layer was washed with water twice
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-14e7ebbafea1498b8b926e4c639bfe19
Source dataset
uspto-grants-2016_02
Patent number
US09249145B2

Reaction notes

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