Triethylamine → (2-Methoxyethoxy)methyl-2-{[1-({[(3s)-1-(2-tert.butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1h-1-benzazepin-3-yl]amino}carbonyl)cyclopentyl]methyl}-4-(isopropylamino)-4-oxobutyric acid

HRID 32355

反応式

HRID 32355 の反応式
[C:1]([O:5][C:6](=[O:40])[CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][C@H:10]([NH:19][C:20]([C:22]2([CH2:27][CH:28]([CH2:32][C:33]([NH:35][CH:36]([CH3:38])[CH3:37])=[O:34])[C:29]([OH:31])=[O:30])[CH2:26][CH2:25][CH2:24][CH2:23]2)=[O:21])[C:9]1=[O:39])([CH3:4])([CH3:3])[CH3:2].[CH3:41][O:42][CH2:43][CH2:44][O:45][CH2:46]Cl.C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[CH3:41][O:42][CH2:43][CH2:44][O:45][CH2:46][C:28]([CH2:27][C:22]1([C:20]([NH:19][C@H:10]2[CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:8]([CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:40])[C:9]2=[O:39])=[O:21])[CH2:26][CH2:25][CH2:24][CH2:23]1)([CH2:32][C:33]([NH:35][CH:36]([CH3:37])[CH3:38])=[O:34])[C:29]([OH:31])=[O:30]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 589354242-{[1-({[(3S)-1-(2-tert. butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}-carbonyl)cyclopentyl]methyl}-4-(isopropylamino)-4-oxobutyric Acid

生成物 1

HCID 69272815(2-Methoxyethoxy)methyl-2-{[1-({[(3s)-1-(2-tert.butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1h-1-benzazepin-3-yl]amino}carbonyl)cyclopentyl]methyl}-4-(isopropylamino)-4-oxobutyric acid

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

300 mg 2-{[1-({[(3S)-1-(2-tert.butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}-carbonyl)cyclopentyl]methyl}-4-(isopropylamino)-4-oxobutyric acid (for preparation see Example 12) was dissolved in 5 ml dichloromethane. 33 mg DMAP, 74 μl methoxyethoxymethyl chloride and 90 μl triethylamine were added to this receiving solution. The reaction mixture was stirred overnight, then diluted with 5 ml dichloromethane and the organic phase was washed in succession once each with 3 ml dilute aqueous KHSO4 solution and saturated aqueous common salt solution. The organic phase was dried over magnesium sulfate, the solvent was largely evaporated at reduced pressure and the remaining residue was chromatographed on silica gel (mobile phase: EA/cyclohexane 2:1 v/v). Drying the product fractions in an oil pump vacuum yielded 191 g of the title compound, MS: [M+H]+: 646; m/z: 590, 540, 484, 425.

後処理

  1. washthe organic phase was washed in succession once each with 3 ml dilute aqueous KHSO4 solution and saturated aqueous common salt solution
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customthe solvent was largely evaporated at reduced pressure
  4. customthe remaining residue was chromatographed on silica gel (mobile phase: EA/cyclohexane 2:1 v/v)
  5. customDrying the product fractions in an oil pump vacuum

出典と根拠

ORDレコード
ord-8a6b5cd84c4a4679bc4fa08bef6346bc
出典データセット
uspto-grants-2008_09
特許番号
US07427611B2

関連ノート

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