Hydrochloric Acid → Ammonia

HRID 1433245Notes

Reaction equation

HRID 1433245 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([C@@H:27]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH2:28][CH2:29][N:30]([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])[CH:21]=2)=[CH:12][CH:11]=1)(C)(C)C.Cl>ClCCl.C(OCC)C>[NH3:7].[NH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([C@@H:27]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH2:28][CH2:29][N:30]([CH:34]([CH3:35])[CH3:36])[CH:31]([CH3:33])[CH3:32])[CH:21]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 57933235tert-Butyl{2-[4-(3-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}propoxy)phenyl]ethyl}carbamate

Product 2

HCID 222AmmoniaHCID 579331574-{3-[4-(2-aminoethyl)phenoxy]propyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

tert-Butyl{2-[4-(3-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}propoxy)phenyl]ethyl}carbamate (Preparation 7, 400 mg, 0.68 mmol) was dissolved in dichloromethane (15 ml) and hydrochloric acid (10 ml of a 2M solution in diethyl ether) was added to the stirred solution at 0° C. After 3 hours the solvent was removed in vacuo, and ethyl acetate (20 ml) and saturated aqueous sodium hydrogen carbonate (10 ml) were added and the organics separated. The aqueous was washed with dichloromethane:methanol (90:10, by volume, 2×20 ml) and the organics combined, dried (magnesium sulphate) and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (80/20/2.0 by volume) to furnish the title compound as a glass, 135 mg.

Workup

  1. customAfter 3 hours the solvent was removed in vacuo, and ethyl acetate (20 ml) and saturated aqueous sodium hydrogen carbonate (10 ml)
  2. additionwere added
  3. washThe aqueous was washed with dichloromethane:methanol (90:10, by volume, 2×20 ml)
  4. dry with materialdried (magnesium sulphate)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-dc2cd6ec453041a897b37f67287270a2
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

Loading…