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

HRID 1254347Notes

Reaction equation

HRID 1254347 reaction equation
C(OC([NH:8][C@@H:9]([CH2:23][CH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1)[CH2:10][N:11]([CH3:22])[C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O)(C)(C)C.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:8][C@@H:9]([CH2:23][CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28]1)[CH2:10][N:11]([CH3:22])[C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 59383026benzyl (S)-2-(t-butoxycarbonylamino)-3-cyclopentylpropylmethylcarbamate

Product 1

HCID 59382929benzyl (S)-2-amino-3-cyclopentylpropylmethylcarbamateYield 102.7%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of benzyl (S)-2-(t-butoxycarbonylamino)-3-cyclopentylpropylmethylcarbamate (550 mg) in TFA/CH2Cl2 (10 mL, 20% v/v) was stirred for 2 h at 5° C. The mixture was neutralized with sat'd aq NaHCO3 and extracted with CH2Cl2 (3×30 mL). The combined organic extracts were washed with brine (30 mL), dried over Na2SO4 and evaporated to give benzyl (S)-2-amino-3-cyclopentylpropylmethylcarbamate (420 mg) that was used in the next step without further purification.

Workup

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

Sources & evidence

ORD record
ord-bf9a3c4c31ea438e8dfd6f9ea3fdbc5c
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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