Butyramide → HCID 60105793, 화합물

HRID 1837641

반응식

HRID 1837641 반응식
CS(O[CH2:6][CH:7]1[CH2:11][C:10](=[O:12])[N:9]([C@H:13]([C:16]([NH2:18])=[O:17])[CH2:14][CH3:15])[CH2:8]1)(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+].FCC1CN([C@@H](CC)C(N)=O)C(=O)C1.O=C1CC(CN2C=NN=N2)CN1[C@@H](CC)C(N)=O.O=C(CCN1CCCC1CN1C=NC=N1)C(N)=O.O=C1CC(CN2C=CN=N2)CN1C(CC)C(N)=O.C(SCC1CN([C@@H](CC)C(N)=O)C(=O)C1)(C)C.C(N)(=O)CCC.O=C1CC(CN2CCSCC2)CN1[C@@H](CC)C(N)=O>C(#N)C>[N:19]([CH2:6][CH:7]1[CH2:8][N:9]([C@@H:13]([CH2:14][CH3:15])[C:16]([NH2:18])=[O:17])[C:10](=[O:12])[CH2:11]1)=[N+:20]=[N-:21]

참가 물질

11

반응물 9

HCID 10927ButyramideHCID 33557Sodium Azide2회HCID 9813710(2S)-2-[2-oxo-4-(1H-tetrazol-1-ylmethyl)-1-pyrrolidinyl]butanamide2회HCID 223871002-[2-oxo-4-(1H-1,2,3-triazol-1-ylmethyl)-1-pyrrolidinyl]butanamideHCID 57478742HCID 57478742, 화합물HCID 57478744HCID 57478744, 화합물HCID 66725879(2S)-2-[2-oxo-4-(4-thiomorpholinylmethyl)-1-pyrrolidinyl]butanamideHCID 66725939(2S)-2-[4-(fluoromethyl)-2-oxo-1-pyrrolidinyl]butanamideHCID 1317245752-oxo-4-(1H-1,2,4-triazol-1-ylmethyl-pyrrolidinyl]butanamide

생성물 1

HCID 60105793HCID 60105793, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

반응 조건

온도
10 °C

실험 절차

In a 3 l three necked flask fitted with mechanical stirrer and reflux condenser, under inert atmosphere, 89.7 g (322 mmoles, 1 eq) of {1-[(1S)-1-(aminocarbonyl)propyl]-5-oxo-3-pyrrolidinyl}methyl methanesulfonate 37 are dissolved in 300 ml of acetonitrile. 27.3 g (419 mmoles, 1.3 eq) of sodium azide are added in one portion, with 150 ml of acetonitrile. The mixture is brought to reflux in 20 min, and stirred overnight. 3.1 g (48 mmoles, 0.2 eq) of sodium azide are added and reflux continued for a total of 44 hours. After cooling down to 10° C., the mixture is filtered, the precipitate washed with 3×50 ml of acetonitrile and the combined organic fractions concentrated to dryness to give 77.3 g of crude 32. It is crystallised from 150 ml of ethyl acetate at 10° C. to give 60 g of pure 32, 82%. Alternatively, (2S)-2-[4-(fluoromethyl)-2-oxo-1-pyrrolidinyl]butanamide 44, (2S)-2-[-2-oxo-4-(1H-tetrazol-1-ylmethyl)-1-pyrrolidinyl]butanamide 39, (2S)-2-[2-oxo-4-(1H-tetrazol -1-ylmethyl)-1-pyrrolidinyl]butanamide 40, (2S)-2-[2-oxo-4-(1H-1,2,4-triazol-1-ylmethyl -pyrrolidinyl]butanamide 55, 2-[2-oxo-4-(1H-1,2,3-triazol-1-ylmethyl)-1-pyrrolidinyl]butanamide 56, (2S)-2-{4-[(isopropylsulfanyl)methyl]-2-oxo-1-pyrrolidinyl}butanamide 24, (2S)-4-(1-pyrrolidinylmethyl)-1-pyrrolidinyl]butanamide 15, (2S)-2-[2-oxo-4-(4-thiomorpholinylmethyl)-1-pyrrolidinyl]butanamide 17, are prepared in similar ways, from activated alcohol derivatives, such as mesylates, tosylates or halides.

후처리

  1. temperaturereflux condenser
  2. temperatureto reflux in 20 min
  3. temperaturereflux
  4. customcontinued for a total of 44 hours
  5. filtrationthe mixture is filtered
  6. washthe precipitate washed with 3×50 ml of acetonitrile
  7. concentrationthe combined organic fractions concentrated to dryness
  8. customto give 77.3 g of crude 32
  9. customIt is crystallised from 150 ml of ethyl acetate at 10° C.
  10. customto give 60 g of pure 32, 82%

출처 및 근거

ORD 기록
ord-15c01d2213d1436bb3f3a8f0e7b6ba34
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06784197B2

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