p-Toluenesulfonic acid → HCID 86626197, compound

HRID 2355485Notes

Reaction equation

HRID 2355485 reaction equation
[CH3:1][O:2][C:3]([CH3:27])([CH3:26])[CH2:4][C@H:5]([NH:18]C(=O)OC(C)(C)C)[CH2:6][N:7]([CH3:17])[C:8]([O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14])=[O:9].C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC.C(O)C>[NH2:18][C@@H:5]([CH2:4][C:3]([O:2][CH3:1])([CH3:27])[CH3:26])[CH2:6][N:7]([CH3:17])[C:8](=[O:9])[O:10][CH2:11][CH2:12][Si:13]([CH3:15])([CH3:14])[CH3:16]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acid2×HCID 86626198HCID 86626198, compound

Product 1

HCID 86626197HCID 86626197, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
62.5 °C

Procedure

To a solution of (S)-tert-butyl 4-methoxy-4-methyl-1-(N-methyl-N-(2-(trimethylsilyl)-ethoxycarbonyl)amino)pentan-2-ylcarbamate (0.17 g, 0.42 mmol) in ether (2.0 mL) was added a solution of p-toluenesulfonic acid (80.7 mg, 0.43 mmol) in ethanol (1.0 mL). Transfer of the p-toluenesulfonic acid was completed with the aid of additional ether (1.0 mL). The solution was placed on a rotary evaporator and the ether was removed at rt. Then, with continuing evacuation, the bath temperature was raised to 60-65° C. for 20 min, during which gas evolution was evident. After cooling down to rt, the solid residue (S)-2-(trimethylsilyl)ethyl 2-amino-4-methoxy-4-methylpentyl(methyl)-carbamate was used without further purification as a p-toluenesulfonic acid salt. MS m/z 291 (M+H+).

Workup

  1. customThe solution was placed on a rotary evaporator
  2. customthe ether was removed at rt
  3. temperatureAfter cooling down to rt
  4. customthe solid residue (S)-2-(trimethylsilyl)ethyl 2-amino-4-methoxy-4-methylpentyl(methyl)-carbamate was used without further purification as a p-toluenesulfonic acid salt

Sources & evidence

ORD record
ord-d699f67cad7d4f7b8451b92f3dba36c2
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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