Hydrochloric Acid → HCID 22644926, compound

HRID 2268288Notes

Reaction equation

HRID 2268288 reaction equation
[C:1](=[O:4])([O-])[O-:2].[Na+].[Na+].[CH2:7]([O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1)[C:8]#[C:9][CH3:10].Cl.C[N:24]([CH3:27])C=O>C(OCC)(=O)C.O>[CH2:7]([O:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:24][C:27]2([C:1]([OH:2])=[O:4])[CH2:10][CH2:9][CH2:8][CH2:7]2)(=[O:20])=[O:19])=[CH:14][CH:13]=1)[C:8]#[C:9][CH3:10]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 111959284-But-2-ynyloxy-benzenesulfonyl chloride

Product 1

HCID 22644926HCID 22644926, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of cis-2-amino-1-cyclopentane (1.0 g, 7.74 mmol) in 1:1 water:dimethylformamide (10 mL) at 0° C. was added sodium carbonate (2.7 g, 25.5 mmol) followed by 4-(2-butynyloxy)phenyl sulfonyl chloride (2.08 g, 8.5 mmol). The reaction mixture was allowed to warm to room temperature. After stirring overnight water and ethyl acetate were added and the mixture acidified to pH=1 with 6N aqueous hydrochloric acid. The organic phase was washed with water and brine and dried over anhydrous sodium sulfate. Filtration and concentration in vacuo gave (1R,2S)-2-[{[4-(2-butynyloxy)phenyl]sulfonyl}amino cyclopentanecarboxylic acid (1.58 g) as a white solid, mp 105-135° C. Electrospray Mass Spec 336.4 (M+H)+.

Workup

  1. additionwere added
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-0c84a64574a240c0a8d45282c4614745
Source dataset
uspto-grants-2001_12
Patent number
US06326516B1

Reaction notes

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