Benzaldehyde, 4-octyl- → HCID 178442644、化合物

HRID 898213ノート

反応式

HRID 898213 の反応式
[NH2:1][CH2:2][CH:3]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:4][P:5](C(OCC)OCC)(=[O:9])[O:6]CC.[CH2:23]([C:31]1[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CO>[CH2:23]([C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH:1][CH2:2][CH:3]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:4][PH:5](=[O:9])[OH:6])=[CH:33][CH:32]=1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

参加物

4

反応物 2

HCID 2734685Benzaldehyde, 4-octyl-HCID 14362832Ethyl 3-amino-2-phenylpropyl(diethoxymethyl)phosphinate

生成物 1

HCID 178442644HCID 178442644、化合物収率 26.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 69.2 mg (0.210 mmol) of ethyl 3-amino-2-phenylpropyl(diethoxymethyl)phosphinate (Tetrahedron, 1989, 3787-3808) and 48.2 mg (0.221 mmol) of 4-octylbenzaldehyde in 1 mL of MeOH at rt was treated with 6.7 mg (0.105 mmol) of Na(CN)BH3. The resulting reaction mixture was stirred at rt for 16 hr. The reaction was quenched with 0.3 mL of 12 N HCl, then heated up to 60° C. for 5 hr. The mixture was cooled and concentrated. HPLC purification (LC-2) afforded 22 mg (26%) of the title compound. 1H NMR (500 MHz) (CD3OD) δ 0.88 (t, J=7.1, 3H), 1.26-1.30 (m, 10H), 1.58-1.61 (m, 2H), 2.01-2.17 (m, 2H), 2.62 (t, J=7.8, 2H), 3.20-3.23 (m, 1H),3.35-3.46 (m, 2H), 4.11 (s, 2H), 6.92 (d, J=535.4, 1H), 7.23-7.37 (m, 9H); LC-1: 3.31 min; ESI-MS 402 (M+H).

後処理

  1. customThe resulting reaction mixture
  2. customThe reaction was quenched with 0.3 mL of 12 N HCl
  3. temperatureheated up to 60° C. for 5 hr
  4. temperatureThe mixture was cooled
  5. concentrationconcentrated
  6. customHPLC purification (LC-2)

出典と根拠

ORDレコード
ord-ac18f86ffd9b427091b42427475c7bf7
出典データセット
uspto-grants-2008_04
特許番号
US07351725B2

反応ノート

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