Hydrochloric Acid → Ammonia

HRID 1433240Notes

Reaction equation

HRID 1433240 reaction equation
Cl.C(OC([N:9]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]=[CH:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:29]([C@@H:41]([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[CH2:42][CH2:43][N:44]([CH:48]([CH3:50])[CH3:49])[CH:45]([CH3:47])[CH3:46])[CH:28]=1)C(OC(C)(C)C)=O)=O)(C)(C)C>C(OCC)C.ClCCl>[NH3:9].[CH2:34]([O:33][C:30]1[CH:31]=[CH:32][C:27]([CH:26]=[CH:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][NH2:9])=[CH:28][C:29]=1[C@@H:41]([C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[CH2:42][CH2:43][N:44]([CH:45]([CH3:46])[CH3:47])[CH:48]([CH3:50])[CH3:49])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 68930431di-tert-butyl[10-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}dec-9-en-1-yl]imidodicarbonate

Product 2

HCID 222AmmoniaHCID 6893123410-{4-(Benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}dec-9-en-1-amine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Hydrochloric acid (10.0 ml of a 2M solution in diethyl ether) was added in one portion to a stirred solution of di-tert-butyl[10-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}dec-9-en-1-yl]imidodicarbonate (Preparation 2, 450 mg, 0.59 mmol) at room temperature in dichloromethane (5 ml) under a nitrogen atmosphere. The reaction was stirred for 2 hours and the solvent removed in vacuo, the residue was dissolved in ethyl acetate (30 ml) and saturated aqueous sodium hydrogen carbonate (20 ml). The organics were separated, washed with water (10 ml), 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 (90/10/1.0 by volume) to furnish the title compound as a glass, 180 mg.

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (30 ml)
  3. customThe organics were separated
  4. washwashed with water (10 ml)
  5. dry with materialdried (magnesium sulphate)
  6. customthe solvent removed in vacuo
  7. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-bab627d9c06a461db6dd318f8dc6bead
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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