Hydrochloric Acid → methyl (1S)-1-[({(1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-[4-(6-methoxy-2-pyridinyl)phenyl]pentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate

HRID 1174325Notes

Reaction equation

HRID 1174325 reaction equation
[OH:1][C@@H:2]([CH2:30][C@@H:31]([NH:39][C:40](=[O:51])[C@@H:41]([NH:46][C:47]([O:49][CH3:50])=[O:48])[C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C@@H:3]([NH:19]C(=O)OCC1C=CC=CC=1)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[N:12]=2)=[CH:7][CH:6]=1.Cl>CO.[Pd]>[NH2:19][C@@H:3]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[N:12]=2)=[CH:9][CH:10]=1)[C@@H:2]([OH:1])[CH2:30][C@@H:31]([NH:39][C:40]([C@@H:41]([NH:46][C:47](=[O:48])[O:49][CH3:50])[C:42]([CH3:44])([CH3:45])[CH3:43])=[O:51])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86726228benzyl (1S,2S,4S)-2-hydroxy-4-({(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoyl}amino)-1-[4-(6-methoxy-2-pyridinyl)benzyl]-5-phenylpentylcarbamate

Product 1

HCID 86726227methyl (1S)-1-[({(1S,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-[4-(6-methoxy-2-pyridinyl)phenyl]pentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution containing the product from Example 120A (0.028 g, 0.041 mmol) in methanol (1 mL) was treated with 10% Pd on carbon (0.003 g) and HCl solution (0.030 mL, 4 N in dioxane), and the reaction was stirred under a hydrogen atmosphere (balloon pressure) at 25° C. for 16 hours. The reaction was filtered through a bed of celite and rinsed with methanol. The solvent was concentrated to give the title compound as the hydrochloride salt, which was used without further purification.

Workup

  1. filtrationThe reaction was filtered through a bed of celite and
  2. washrinsed with methanol
  3. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-44a981a8ef3d438cbfdc1e92725242b6
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

Loading…