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

HRID 490932

反応式

HRID 490932 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-038668abce88414ba18426d9f343faca
出典データセット
uspto-grants-2009_05
特許番号
US07528173B2

関連ノート

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