Hydrochloric Acid → tert-butyl (1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-[4-(3-pyridinyl)phenyl]pentylcarbamate

HRID 1174229Notes

Reaction equation

HRID 1174229 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[CH2:10][C@@H:11]1[O:15]C(C)(C)[N:13](C(OCC2C=CC=CC=2)=O)[C@H:12]1[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=2)=[CH:31][CH:30]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>CO.[OH-].[OH-].[Pd+2]>[NH2:13][C@@H:12]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=2)=[CH:31][CH:30]=1)[C@@H:11]([OH:15])[CH2:10][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 56594883benzyl (4S,5S)-5-{(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropyl}-2,2-dimethyl-4-[4-(3-pyridinyl)benzyl]-1,3-oxazolidine-3-carboxylate

Product 1

HCID 86726190tert-butyl (1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-[4-(3-pyridinyl)phenyl]pentylcarbamate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution containing the product from Example 67A (0.130 g, 0.205 mmol) in methanol (3 mL) was treated with Pd(OH)2 on carbon (0.040 g, 20% Pd by wt.) and HCl solution (0.150 mL, 4N in dioxane), stirred under a hydrogen atmosphere (balloon pressure) for 2.5 hours at 25° C., filtered through a bed of celite® and rinsed with methanol. The filtrate was concentrated to give the title compound as the hydrochloride salt.

Workup

  1. filtrationfiltered through a bed of celite®
  2. washrinsed with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c08ff1501e9a4ddab643ac2bf285d599
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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