Trifluoroacetic acid → methyl (1S)-2-methyl-1-({2-[4-(2-pyridinyl)benzyl]hydrazino}carbonyl)propylcarbamate
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:22]=[CH:21][C:10]([CH2:11][NH:12][NH:13][C:14]([O:16]C(C)(C)C)=O)=[CH:9][CH:8]=1.FC(F)(F)[C:25]([OH:27])=[O:26].[CH:30](N(C(C)C)CC)(C)C.CCOP(O[N:48]1N=N[C:52]2C=CC=[CH:56][C:51]=2[C:49]1=O)(OCC)=O>ClCCl>[CH3:52][CH:51]([CH3:56])[C@H:49]([NH:48][C:25](=[O:26])[O:27][CH3:30])[C:14]([NH:13][NH:12][CH2:11][C:10]1[CH:9]=[CH:8][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[CH:22][CH:21]=1)=[O:16]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of Example 4B (0.18 g, 0.6 mmol) in dichloromethane:trifluoroacetic acid (4 mL, 1:1) was stirred at 25° C. for 1 h, and the solvents were evaporated. This material was dissolved in THF (1 mL) and treated with diisopropylethyl amine (0.31 mL, 3 equivalents), DEPBT (0.36 g, 2 equivalents), and Example 18A (0.105 g, 1 equivalent), stirred at 25° C. for 3 h. The mixture was partitioned between dichloromethane and 10% sodium carbonate, the organic layer was separated, washed with brine, dried over sodium sulfate, filtered and the solvents were evaporated. The crude residue was purified using 2% methanol/chloroform to give 0.1 g (47%) of the title compound.
Workup
- customthe solvents were evaporated
- dissolutionThis material was dissolved in THF (1 mL)
- customThe mixture was partitioned between dichloromethane and 10% sodium carbonate
- customthe organic layer was separated
- washwashed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customthe solvents were evaporated
- customThe crude residue was purified
Sources & evidence
- ORD record
- ord-78d62214a5224b799cfb2c7563973491
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07696226B2
Reaction notes
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