Benzyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-(3-hydroxyadamantan-1-yl)-2-oxo ethyl]carbamate → Saxagliptin

HRID 1184043

반응식

HRID 1184043 반응식
[C:1]([C@@H:3]1[CH2:8][C@H:7]2[C@H:5]([CH2:6]2)[N:4]1[C:9](=[O:33])[C@@H:10]([NH:22]C(=O)OCC1C=CC=CC=1)[C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][C:13]([OH:21])([CH2:14]3)[CH2:12]1)[CH2:18]2)#[N:2]>CO>[CH2:8]1[C@@H:3]([C:1]#[N:2])[N:4]([C:9]([C@@H:10]([NH2:22])[C:11]23[CH2:12][C:13]4([OH:21])[CH2:19][CH:17]([CH2:16][CH:15]([CH2:14]4)[CH2:20]2)[CH2:18]3)=[O:33])[C@@H:5]2[C@H:7]1[CH2:6]2

참가 물질

3

반응물 1

HCID 86703399Benzyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-(3-hydroxyadamantan-1-yl)-2-oxo ethyl]carbamate

생성물 1

HCID 11243969Saxagliptin

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of benzyl N-[(1S)-2-[(1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl]-1-(3-hydroxyadamantan-1-yl)-2-oxo-ethyl]carbamate (10 gm) (formula-IX) in methanol 5% Pd/C (50% wet, 1 gm) was added. Hydrogen gas was bubbled through the reaction mass for 2 hrs at 20-25° C. After the starting material was completely converted, the reaction mass was filtered. The filtrate was evaporated to yield SAXAGLIPTIN free base of formula-I as a foamy solid. To the solid ethyl acetate (5 ml), 20 micro liters of water and n-hexane (20 ml) were added, stirred at 0-5° C. and filtered the white solid formed to yield 6.98 gm (94%) of SAXAGLIPTIN MONO HYDRATE. HPLC Purity: 99.5% (A) and the content of the impurity cyclic amidine: 0.09% (A), M.P: 105-108° C.

후처리

  1. customHydrogen gas was bubbled through the reaction mass for 2 hrs at 20-25° C
  2. filtrationthe reaction mass was filtered
  3. customThe filtrate was evaporated

출처 및 근거

ORD 기록
ord-694e15cf6b7e439cacb5e710e5630d2a
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664443B2

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