Hydrochloric Acid → benzyl (1S,2S,4S)-4-amino-2-hydroxy-1-[4-(6-methoxy-2-pyridinyl)benzyl]-5-phenylpentylcarbamate

HRID 1174324Notes

Reaction equation

HRID 1174324 reaction equation
C(OC([NH:8][C@@H:9]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:10][C@@H:11]1[O:15]C(C)(C)[N:13]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[C@H:12]1[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH3:42])[N:36]=2)=[CH:31][CH:30]=1)=O)(C)(C)C.Cl>C1COCC1.O1CCOCC1>[NH2:8][C@@H:9]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:10][C@H:11]([OH:15])[C@@H:12]([NH:13][C:18](=[O:19])[O:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH3:42])[N:36]=2)=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67407029benzyl (4S,5S)-5-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl]-4-[4-(6-methoxy-2-pyridinyl)benzyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Product 1

HCID 86599578benzyl (1S,2S,4S)-4-amino-2-hydroxy-1-[4-(6-methoxy-2-pyridinyl)benzyl]-5-phenylpentylcarbamate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A solution containing the product from Example 119A (0.095 g, 0.14 mmol) in THF (1 mL) was treated with a solution of HCl in dioxane (0.25 mL, 4 N), stirred at 50° C. for 16 hours, cooled and concentrated under reduced pressure. The residue was dissolved in ethanol and concentrated several times to give the title compound as hydrochloride salt, which was used without further purification.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethanol
  4. concentrationconcentrated several times

Sources & evidence

ORD record
ord-8140fe0f28e54b449f4ce32c7a315b89
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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