Chlorotrimethylsilane → 1-(2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-3-(p-nitrophenoxycarbonylamino)propyl)-1-(trimethylsilyloxy)cyclohexane

HRID 1254323Notes

Reaction equation

HRID 1254323 reaction equation
[NH2:1][CH2:2][CH:3]([N:12]([CH3:22])[C:13]([O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])=[O:14])[CH2:4][C:5]1([OH:11])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.CCN(CC)CC.[Si:30](Cl)([CH3:33])([CH3:32])[CH3:31].Cl[C:36]([O:38][C:39]1[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=1)=[O:37]>C(Cl)Cl>[CH3:22][N:12]([CH:3]([CH2:2][NH:1][C:36]([O:38][C:39]1[CH:40]=[CH:41][C:42]([N+:45]([O-:47])=[O:46])=[CH:43][CH:44]=1)=[O:37])[CH2:4][C:5]1([O:11][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[C:13]([O:15][CH2:16][CH2:17][Si:18]([CH3:20])([CH3:19])[CH3:21])=[O:14]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 671900581-(3-amino-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propyl)cyclohexanol

Product 1

HCID 671916311-(2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-3-(p-nitrophenoxycarbonylamino)propyl)-1-(trimethylsilyloxy)cyclohexane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-amino-2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-propyl)cyclohexanol (21 mg, 0.064 mmol) in CH2Cl2 (2 mL) were added Et3N (0.2 mL) and Me3SiCl (13.9 mg, 16 μL, 0.13 mmol). The resulting solution was stirred for 1 h and evaporated under vacuum. The residue was dissolved in CH2Cl2 (2 mL) and pyridine (0.05 mL) was added, followed by 4-nitrophenyl chloroformate (15 mg, 0.077 mmol). The mixture was stirred for 30 min to afford a solution of 1-(2-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-3-(p-nitrophenoxycarbonylamino)propyl)-1-(trimethylsilyloxy)cyclohexane which was used directly without isolation.

Workup

  1. customevaporated under vacuum
  2. dissolutionThe residue was dissolved in CH2Cl2 (2 mL)
  3. additionpyridine (0.05 mL) was added
  4. stirringThe mixture was stirred for 30 min

Sources & evidence

ORD record
ord-c4774b81703a4b5ea4420965824ffa75
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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