Triethylamine → HCID 59134554, compound

HRID 1993497Notes

Reaction equation

HRID 1993497 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][C:10]([OH:18])([CH2:11]3)[CH2:9]1)[CH2:15]2)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH3:27][S:28]([O:18][C:10]12[CH2:16][CH:14]3[CH2:13][CH:12]([CH2:17][C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:19])([CH2:15]3)[CH2:9]1)[CH2:11]2)(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59134555HCID 59134555, compound

Product 1

HCID 59134554HCID 59134554, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5.6 g (21 mmole) of tert-butyl(3-hydroxy-1-adamantyl)carbamate are dissolved in 80 ml of dichloromethane, 4.4 ml (31.5 mmole) of triethylamine are added to it. The mixture is cooled to 0° C. and 1.82 ml (23.5 mmole) of methanesulphonyl chloride is added to it dropwise. The reaction mixture is stirred at that temperature for 45 minutes, then washed consecutively with water and saturated sodium hydrogen carbonate solution. The organic phase is dried over sodium sulphate, evaporated, the residue is purified by column chromatography (n-hexane—ethyl acetate—chloroform 2:1:1) and crystallised from n-hexane, to obtain 2.9 g (40%) of product: Mp.: 100-102° C. 1H-NMR (DMSO-d6): 1.37 (s, 9H), 1.48 (s, 2H), 1.77 (q, 4H), 2.05 (t, 4H), 2.17 (d, 2H), 3.10 (s, 3H), 6.66 (s, 1H).

Workup

  1. washwashed consecutively with water and saturated sodium hydrogen carbonate solution
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. customevaporated
  4. customthe residue is purified by column chromatography (n-hexane—ethyl acetate—chloroform 2:1:1)
  5. customcrystallised from n-hexane

Sources & evidence

ORD record
ord-f3f639146e054ed9a3e224a27f840e76
Source dataset
uspto-grants-2010_01
Patent number
US07652021B2

Reaction notes

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