Trifluoroacetic acid → methyl (1S)-1-[({(1S,3S,4S)-4-amino-3-hydroxy-1-[4-(5-methyl-2-pyridinyl)benzyl]-5-phenylpentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate

HRID 1174268Notes

Reaction equation

HRID 1174268 reaction equation
[CH2:1]([C@H:8]([NH:40]C(=O)OC(C)(C)C)[C@@H:9]([OH:39])[CH2:10][C@@H:11]([NH:26][C:27](=[O:38])[C@@H:28]([NH:33][C:34]([O:36][CH3:37])=[O:35])[C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[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>[NH2:40][C@@H:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@@H:9]([OH:39])[CH2:10][C@@H:11]([NH:26][C:27]([C@@H:28]([NH:33][C:34](=[O:35])[O:36][CH3:37])[C:29]([CH3:32])([CH3:31])[CH3:30])=[O:38])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86726214tert-butyl (1S,2S,4S)-1-benzyl-2-hydroxy-4-({(2S)-2-[(methoxycarbonyl)amino]-3,3-dimethylbutanoyl}amino)-5-[4-(5-methyl-2-pyridinyl)phenyl]pentylcarbamate

Product 1

HCID 86726213methyl (1S)-1-[({(1S,3S,4S)-4-amino-3-hydroxy-1-[4-(5-methyl-2-pyridinyl)benzyl]-5-phenylpentyl}amino)carbonyl]-2,2-dimethylpropylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution containing the product from Example 92I (0.120 g, 0.183 mmol) in dichloromethane (1 mL) was treated with trifluoroacetic acid (1 mL), stirred at 25° C. for 1 hour. The solvent was concentrated and the mixture was partitioned between chloroform and saturated NaHCO3 solution. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated, and the crude product (0.098 g) was used without further purification.

Workup

  1. concentrationThe solvent was concentrated
  2. customthe mixture was partitioned between chloroform and saturated NaHCO3 solution
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe crude product (0.098 g) was used without further purification

Sources & evidence

ORD record
ord-98aeaaf7e7944647bb37e12f241c9ff8
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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