Water → 2-(R)-Amino-3-(R)-benzyloxy-5-(3-benzyloxyphenyl)-4-(S)-dibenzylaminopentan-1-ol

HRID 20350Notes

Reaction equation

HRID 20350 reaction equation
C(OC([N:8]1[C@@H:12]([C@@H:13]([O:45][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C@@H:14]([N:30]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:17]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C.O.C(=O)(O)[O-].[Na+]>Cl.O1CCOCC1>[NH2:8][C@@H:12]([C@@H:13]([O:45][CH2:46][C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1)[C@@H:14]([N:30]([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:17]=1)[CH2:11][OH:10]

Participants

6

Reactant 3

HCID 962Water2×HCID 516892Sodium BicarbonateHCID 685579764-(R)-[1-(S)-benzyloxy-3-(3-benzyloxyphenyl)-2-(S)-dibenzylaminopropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 685587952-(R)-Amino-3-(R)-benzyloxy-5-(3-benzyloxyphenyl)-4-(S)-dibenzylaminopentan-1-ol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Dissolve 4-(R)-[1-(S)-benzyloxy-3-(3-benzyloxyphenyl)-2-(S)-dibenzylaminopropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (16.01 g, 22.0 mmol) in 4 M hydrogen chloride in 1,4-dioxane (130 mL) and stir for 30 minutes. Add water (65 mL) and stir for 18 hours. Slowly add sodium bicarbonate (50 g) and water (˜50 mL). Extract with ethyl acetate, wash with saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate to give the crude desired compound.

Workup

  1. extractionExtract with ethyl acetate
  2. washwash with saturated aqueous sodium chloride
  3. dry with materialdry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-29601f73a49241d690cf70d5de7a0301
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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