Butyramide → HCID 60105793、化合物

HRID 393350

反応式

HRID 393350 の反応式
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=C1CC(CN2C=NC=N2)CN1[C@@H](CC)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]

参加物

11

反応物 9

HCID 10927ButyramideHCID 33557Sodium Azide2 回HCID 9813710(2S)-2-[2-oxo-4-(1H-tetrazol-1-ylmethyl)-1-pyrrolidinyl]butanamide2 回HCID 22387100HCID 22387100、化合物HCID 57478742HCID 57478742、化合物HCID 57478743HCID 57478743、化合物HCID 57478744HCID 57478744、化合物HCID 66725879HCID 66725879、化合物HCID 66725939HCID 66725939、化合物

生成物 1

HCID 60105793HCID 60105793、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
10 °C

実験手順

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)-1-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)-2-[2-oxo-4-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.

後処理

  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%

出典と根拠

ORDレコード
ord-8c08c0d3e1f547caaa265cc43d090b32
出典データセット
uspto-grants-2004_10
特許番号
US06806287B2

関連ノート

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