1-Hydroxybenzotriazole → (1-{2-[(2-Isopropyl-5-methyl-cyclohexanecarbonyl)-amino]-1-phenyl-ethylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester

HRID 501475

反応式

HRID 501475 の反応式
[C:1]([NH:8][C@@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:36][CH:37]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH2:38][NH:39][C:40]([CH:42]1[CH2:47][CH:46]([CH3:48])[CH2:45][CH2:44][CH:43]1[CH:49]([CH3:51])[CH3:50])=[O:41]>O.C(OCC)(=O)C.C1COCC1>[C:4]([O:3][C:1](=[O:2])[NH:8][CH:9]([C:11](=[O:13])[NH:36][CH:37]([C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)[CH2:38][NH:39][C:40]([CH:42]1[CH2:47][CH:46]([CH3:48])[CH2:45][CH2:44][CH:43]1[CH:49]([CH3:51])[CH3:50])=[O:41])[CH3:10])([CH3:5])([CH3:6])[CH3:7]

参加物

8

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 637606BOC-D-alanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 668315382-Isopropyl-5-methyl-cyclohexanecarboxylic acid (2-amino-2-phenyl-ethyl)-amide

生成物 1

HCID 66831508(1-{2-[(2-Isopropyl-5-methyl-cyclohexanecarbonyl)-amino]-1-phenyl-ethylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester収率 25.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A 15 mL reaction vessel equipped with a stir bar was charged with THF (15 mL), Boc-(R)-alanine (52 mg, 0.273 mmoles), HOBt (37.87 mg, 0.273 mmoles), EDCl (53 mg, 0.273 mmoles) and TEA (37 μl, 0.273 mmoles). The reaction mixture was stirred for 15 min. whereupon 2-isopropyl-5-methyl-cyclohexanecarboxylic acid (2-amino-2-phenyl-ethyl)-amide (75 mg, 0.248 mmol) was added and stirred for an additional 3 h. Ethyl acetate (10 mL) and H2O (10 mL) were added to the reaction mixture. The heterogeneous mixture was transferred to a separatory funnel where the aqueous phase was separated and re-extracted with ethyl acetate (2×10 mL). The organic phases were combined and washed with 1N HCl (2×10 mL), H2O (1×10 mL), sat NaHCO3 (3×10 mL), brine (10 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (20% ethyl acetate/hexane for elution) provided the title compounds as colorless solid (30 mg).

後処理

  1. customA 15 mL reaction vessel
  2. customequipped with a stir bar
  3. additionwas added
  4. customThe heterogeneous mixture was transferred to a separatory funnel
  5. customwhere the aqueous phase was separated
  6. extractionre-extracted with ethyl acetate (2×10 mL)
  7. washwashed with 1N HCl (2×10 mL), H2O (1×10 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by flash chromatography on silica gel (20% ethyl acetate/hexane for elution)

出典と根拠

ORDレコード
ord-c5465a5287dd45deac9da208552ef482
出典データセット
uspto-grants-2010_08
特許番号
US07772266B2

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