1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (2R,5S,6S)-5-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester

HRID 1790622

反応式

HRID 1790622 の反応式
CN(C)CCCN=C=NCC.O.[C:13]([NH:20][C@H:21]([C:26]([OH:28])=O)[CH2:22][CH:23]([CH3:25])[CH3:24])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].OC1C2N=NNC=2C=CC=1.[CH2:39]([O:46][C:47]([N:49]1[CH2:55][CH:54]([OH:56])[CH:53]([NH2:57])[CH2:52][CH2:51][CH:50]1[CH3:58])=[O:48])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C=O)C.CCOC(C)=O>[CH2:39]([O:46][C:47]([N:49]1[CH2:55][C@H:54]([OH:56])[C@@H:53]([NH:57][C:26](=[O:28])[C@@H:21]([NH:20][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:22][CH:23]([CH3:24])[CH3:25])[CH2:52][CH2:51][C@H:50]1[CH3:58])=[O:48])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 12373896N-Boc-L-Leucine HydrateHCID 21036430Racemic (2R,5S,6S)-5-Amino-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl esterHCID 178418300HCID 178418300、化合物

生成物 1

HCID 69000072(2R,5S,6S)-5-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester収率 77.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide (0.164 g, 0.22 mmol) was added to a solution of Boc-Leucine-hydrate (0.190 g, 0.76 mmol), diisopropyletbylamine (0.164 g, 0.22 ml, 1.27 mmol), hydroxybenztriazole (0.114 g, 0.83 mmol), and racemic (2R,5S,6S)-5-Amino-6-hydroxy-2-methyl-azepane-1-carboxylic acid benzyl ester (0.27 g, 0.57 mmol) in DMF (3.2 ml). The reaction was stirred overnight at RT, then was diluted with EtOAc (100 ml), washed with H2O (3×50 ml), brine (50 ml), dried with magnesium sulfate, filtered, concentrated in vacuo by rotary evaporation, and chromatographed (silica gel, 50% EtOAc/hexanes) to yield the title compound (0.218 g, 72%): 1H NMR: 7.40–7.29 (m, 5H), 6.75 (1H, bd), 5.12 (2H, AB), 5.0 (1H, bs), 4.15–3.72 (m, 2H), 3.06 (1H, d), 1.60–1.30 (m, 2H), 1.60–1.30 (m, 5H), 1.12 (3H, d), 0.97–0.87(6H, dd); Electrospray mass spec: M+H+=492.0.

後処理

  1. washwashed with H2O (3×50 ml), brine (50 ml)
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo by rotary evaporation
  5. customchromatographed (silica gel, 50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-ff1d792039b841c7826edddb51f2b6a9
出典データセット
uspto-grants-2006_07
特許番号
US07071184B2

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