Sodium Bicarbonate → benzyl (S)-2-amino-3-cyclopentylpropylmethylcarbamate

HRID 451781Notes

Reaction equation

HRID 451781 reaction equation
[CH:1]1([CH2:6][C@H:7]([NH:20]C(=O)OC(C)(C)C)[CH2:8][N:9]([CH3:19])[C:10]([O:12][CH2:13][CH2:14][Si](C)(C)C)=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:20][C@@H:7]([CH2:6][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)[CH2:8][N:9]([CH3:19])[C:10](=[O:11])[O:12][CH2:13][C:14]1[CH:4]=[CH:5][CH:1]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 68709020(S)-tert-butyl 1-cyclopentyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-ylcarbamate

Product 1

HCID 59382929benzyl (S)-2-amino-3-cyclopentylpropylmethylcarbamateYield 210.7%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of (S)-tert-butyl 1-cyclopentyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-2-ylcarbamate (550 mg) in TFA/CH2Cl2 (10 mL, 20% v/v) was stirred for 2 hrs at 5° C. The reaction was neutralized with saturated aqueous NaHCO3 and extracted with CH2Cl2 (3×30 mL). The combined extracts were washed with saturated brine (30 mL), dried over Na2SO4, and evaporated to give (S)-benzyl 2-amino-3-cyclopentylpropyl(methyl)carbamate (420 mg) that was used without further purification.

Workup

  1. extractionextracted with CH2Cl2 (3×30 mL)
  2. washThe combined extracts were washed with saturated brine (30 mL)
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-41825737cd164aae9144244d87dbd320
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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