Triethylammonium formate → HCID 59201404, compound

HRID 451895Notes

Reaction equation

HRID 451895 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:44])[NH:24][C@@H:25]([CH2:38][CH2:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:26][N:27](C)[C:28](OCC[Si](C)(C)C)=O)[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1.CCN(CC)CC.C(O)=O>CC#N>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([C@@H:17]2[CH2:22][CH2:21][CH2:20][N:19]([C:23](=[O:44])[NH:24][C@@H:25]([CH2:38][CH2:39][C:40]([CH3:42])([CH3:41])[CH3:43])[CH2:26][NH:27][CH3:28])[CH2:18]2)[O:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11084032Triethylammonium formateHCID 68709121methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-5,5-dimethyl-1-(N-methyl-N-(2-trimethylsilylethoxycarbonyl)amino)hexan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate

Product 1

HCID 59201404HCID 59201404, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
55 °C

Procedure

Methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-5,5-dimethyl-1-(N-methyl-N-(2-trimethylsilylethoxycarbonyl)amino)hexan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate was dissolved in CH3CN and treated with 75 mg (0.504 mmol, 4.5 equiv) of TEAF and the mixture heated to 55° C. for 3 h. The solution was evaporated and purified by prep HPLC to afford methyl 2-((R)-(3-chlorophenyl)((R)-1-((S)-5,5-dimethyl-1-(methylamino)hexan-2-ylcarbamoyl)piperidin-3-yl)methoxy)ethylcarbamate.

Workup

  1. customThe solution was evaporated
  2. custompurified by prep HPLC

Sources & evidence

ORD record
ord-d2c0f47d327845d184ac67fa682a2889
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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