Sodium Hydroxide → phenylmethyl {(1S)-1-[(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-ylcarbonyl]-2,2-dimethylpropyl}carbamate

HRID 2098463Notes

Reaction equation

HRID 2098463 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[C@@H:3]([C:15]([N:17]1[CH2:22][C@@H:21]2[CH2:23][C@H:18]1[CH2:19][N:20]2C(OC(C)(C)C)=O)=[O:16])[NH:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[OH-].[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C@H:18]12[CH2:23][C@H:21]([NH:20][CH2:19]1)[CH2:22][N:17]2[C:15]([C@@H:3]([NH:4][C:5](=[O:6])[O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:2]([CH3:31])([CH3:1])[CH3:32])=[O:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 672158231,1-dimethylethyl (1S,4S)-5-(3-methyl-N-{[(phenylmethyl)oxy]carbonyl}-L-valyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 70232205phenylmethyl {(1S)-1-[(1S,4S)-2,5-diazabicyclo[2.2.1]hept-2-ylcarbonyl]-2,2-dimethylpropyl}carbamateYield 94.7%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 1,1-dimethylethyl (1S,4S)-5-(3-methyl-N-{[(phenylmethyl)oxy]carbonyl}-L-valyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (2.5 g, 5.5 mmol) in 30 ml TFA/DCM (20%) was stirred at room temperature for 1 h. The reaction mixture was made basic by addition of sodium hydroxide, then extracted with DCM (3×50 mL). The DCM was dried over anhydrous Na2SO4 and concentrated to give the title compound (1.8 g) as a pale brown oil. LCMS (m/z): 346.1 (M+H).

Workup

  1. extractionextracted with DCM (3×50 mL)
  2. dry with materialThe DCM was dried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8e6cedaef4d64b14a5b2dfae64376e85
Source dataset
uspto-grants-2013_05
Patent number
US08450484B2

Reaction notes

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