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

HRID 1677608

반응식

HRID 1677608 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6ea9d939b9b74e04a2d660d2ee438185
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008325B2

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