Diethyl Ether → HCID 67189074, compound

HRID 2355476Notes

Reaction equation

HRID 2355476 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][C@H:16]([NH:29]C(=O)OC(C)(C)C)[CH2:17][N:18]([CH3:28])[C:19]([O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])=[O:20])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCOCC.CC1C=CC(S(O)(=O)=O)=CC=1.CCOC(C)=O>CCO>[NH2:29][C@@H:16]([CH2:15][CH:12]1[CH2:11][CH2:10][CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3])[CH2:14][CH2:13]1)[CH2:17][N:18]([CH3:28])[C:19](=[O:20])[O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:26])[CH3:27]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 67189729HCID 67189729, compound

Product 1

HCID 67189074HCID 67189074, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-tert-butyl 1-(4-(tert-butyldimethylsilyloxy)cyclohexyl)-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-ylcarbamate (1.9 g, 3.49 mmol) was dissolved into a minimal volume of Et2O (23.4 mL) and added to a solution of TsOH (0.66 g, 3.49 mmol) in absolute EtOH (5 mL). This solution was placed on a rotary evaporator and the Et2O was removed at ambient temperature. The flask was then lowed into the water bath (temperature: 60° C.) and the selective deprotection of the Boc group proceeded concurrent with removal of the remainder of solvent. The reaction was complete after 2 h and gave a pale yellow oil. The residue was dissolved into EtOAc (30 mL) and washed with 1 M aq NaOH (3×5 mL), brine (4×5 mL). The combined organic layers were dried and concentrated to provide (S)-2-(trimethylsilyl)ethyl 2-amino-3-(4-(tert-butyldimethylsilyloxy)cyclohexyl)propyl(methyl)carbamate (1.15 g, 74%). MS (E/Z): 445 (M+H+).

Workup

  1. customThis solution was placed on a rotary evaporator
  2. customthe Et2O was removed at ambient temperature
  3. customwas then lowed into the water bath (temperature: 60° C.)
  4. customthe selective deprotection of the Boc group proceeded concurrent with removal of the remainder of solvent
  5. customgave a pale yellow oil
  6. washwashed with 1 M aq NaOH (3×5 mL), brine (4×5 mL)
  7. customThe combined organic layers were dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-794d722f4ca544d39a90c2b1d9bf0832
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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