Trifluoroacetic acid → (2S,3S,5S)-2,5-diamino-1-phenyl-6-(4-pyridin-2-ylphenyl)hexan-3-ol

HRID 1174342Notes

Reaction equation

HRID 1174342 reaction equation
[CH2:1]([C@H:8]([NH:34]C(=O)OC(C)(C)C)[C@@H:9]([OH:33])[CH2:10][C@@H:11]([NH:25]C(OC(C)(C)C)=O)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:34][C@H:8]([C@@H:9]([OH:33])[CH2:10][C@@H:11]([NH2:25])[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:17][CH:18]=1)[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86726240tert-butyl(1S,2S,4S)-1-benzyl-4-[(tert-butoxycarbonyl)amino]-2-hydroxy-5-[4-(2-pyridinyl)phenyl]pentylcarbamate

Product 1

HCID 67406716(2S,3S,5S)-2,5-diamino-1-phenyl-6-(4-pyridin-2-ylphenyl)hexan-3-olYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution containing the product from Example 133A (0.60 g, 1.07 mmol) in dichloromethane (10 mL) was treated with trifluoroacetic acid (10 mL), stirred at 25° C. for 1 hour, concentrated and partitioned between chloroform and saturated NaHCO3. The organic was dried over Na2SO4, filtered and concentrated to give the title compound (0.386 g, 98% yield).

Workup

  1. concentrationconcentrated
  2. custompartitioned between chloroform and saturated NaHCO3
  3. dry with materialThe organic was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-515e881420e740d59d8aff796ff773e8
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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