Triethylamine → HCID 11291079, compound

HRID 2268284Notes

Reaction equation

HRID 2268284 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[C:8]([OH:10])=[O:9].C(N(CC)CC)C.[C:18]([O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)#[C:19][CH2:20][CH3:21]>O1CCOCC1.O.C(OCC)(=O)C>[CH2:18]([O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:1][C@@H:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]2[C:8]([OH:10])=[O:9])(=[O:31])=[O:30])=[CH:25][CH:24]=1)[C:19]#[C:20][CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2724640trans-2-Aminocyclohexanecarboxylic acidHCID 22644685HCID 22644685, compound

Product 1

HCID 11291079HCID 11291079, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

To a room temperature solution of 1.5 g (10.2 mmol) of trans-2-amino-1-cyclohexylcarboxylic acid in 75 ml of dioxane:H2O (1:1) containing 2.55 ml (18.3 mmol) of triethylamine was added 3.0 g (11.2 mmol) of 4-butynyloxybenzenesulfonyl chloride. The mixture was stirred at 25° C. for 18 h. The resulting mixture was diluted with ethyl acetate and washed with 1N aqueous hydrochloric acid (3×). The organic phase was dried over anhydrous magnesium sulfate and concentrated in vacuo to afford (1R,2R)-2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)cyclohexanecarboxylic acid as a white solid. Electrospray Mass Spec 352.2 (M+H)+

Workup

  1. washwashed with 1N aqueous hydrochloric acid (3×)
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-653d3d03a5fb4d94ae3332cc24c6db31
Source dataset
uspto-grants-2001_12
Patent number
US06326516B1

Reaction notes

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