(R)-1-Phenylpropylamine → (R)-1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acid

HRID 1677608

Reaction equation

HRID 1677608 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([P:16]([OH:18])[OH:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[C@@H](N)C1C=CC=CC=1>C(O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([P:16]([OH:17])[OH:18])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 5324978(R)-1-PhenylpropylamineHCID 213258521-Carbobenzyloxyamino-2-methylpropanephosphonous acid

Product 1

HCID 67375324(R)-1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acidYield 32.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acid (3.4 g, 12.5 mmol) in 20 mL of absolute ethanol was heated to reflux and (R)-(+)-methylbenzylamine (96% ee, 1.5 g, 12.5 mmol) was added. The resulting mixture was diluted with 120 mL of ethyl acetate. The precipitate was filtered off, washed with 100 mL of ethyl acetate and 100 mL of ether, dried in vacuo to afford (R)-1-(benzyloxycarbonylamino)-2-methylpropylphosphonous acid as a white solid (1.1 g) with a rotation [α]D=−10.87° (c=10 mg/mL 9:1 DMF-H2O). This material was found to be 93% ee by chiral HPLC.

Workup

  1. temperatureto reflux
  2. filtrationThe precipitate was filtered off
  3. washwashed with 100 mL of ethyl acetate and 100 mL of ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-6ea9d939b9b74e04a2d660d2ee438185
Source dataset
uspto-grants-2011_08
Patent number
US08008325B2

Linked notes

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