Hydrochloric Acid → 3-(3-{[7-(Benzyl{(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)heptyl]oxy}propyl)benzenesulfonamide

HRID 2118309Notes

Reaction equation

HRID 2118309 reaction equation
[CH2:1]([N:8]([CH2:30][C@@H:31]([C:33]1[CH:44]=[CH:43][C:36]2[O:37]C(C)(C)[O:39][CH2:40][C:35]=2[CH:34]=1)[OH:32])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[C:22]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH2:1]([N:8]([CH2:30][C@H:31]([OH:32])[C:33]1[CH:44]=[CH:43][C:36]([OH:37])=[C:35]([CH2:40][OH:39])[CH:34]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[C:22]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 691987473-{3-[(7-{Benzyl[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}heptyl)oxy]propyl}benzenesulfonamide

Product 1

HCID 692012113-(3-{[7-(Benzyl{(2R)-2-hydroxy-2-[4-hydroxy-3-(hydroxymethyl)phenyl]ethyl}amino)heptyl]oxy}propyl)benzenesulfonamideYield 96.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred, ice-cooled solution of 3-{3-[(7-{Benzyl[(2R)-2-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-hydroxyethyl]amino}heptyl)oxy]propyl}benzenesulfonamide (97.2 g) in IMS (417 ml) was gradually added aqueous 1M hydrochloric acid (417 ml) keeping the temperature below 15° C. The mixture was then stirred at room temperature for ca 5 h. Saturated sodium bicarbonate (417 ml) and ethyl acetate (1000 ml) were then added to the mixture. The organic layer was separated off, washed with water (400 ml), brine (400 ml) and finally dried (Na2SO4). Concentration in vacuo gave the title compound (87.9 g)—LC RT=4.01 min.

Workup

  1. customthe temperature below 15° C
  2. customThe organic layer was separated off
  3. washwashed with water (400 ml), brine (400 ml)
  4. dry with materialfinally dried (Na2SO4)
  5. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-1b402fbd94354dc8a9f850f2f7ab88d6
Source dataset
uspto-grants-2008_10
Patent number
US07442837B2

Reaction notes

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