HCID 21121691、化合物 → [4-(Cholest-5-en-3beta-yloxy)butanoyl]-15-amino-4,7,10,13-tetraoxapentadecanol

HRID 1052951ノート

反応式

HRID 1052951 の反応式
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][CH2:29][CH2:30][CH2:31][C:32]([OH:34])=O)[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[NH2:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH2:48][CH2:49][C:50](O)=[O:51]>>[CH3:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([CH2:24][CH2:25]2)[C@:21]2([CH3:22])[C:16]([CH2:17][C@@H:18]([O:28][CH2:29][CH2:30][CH2:31][C:32]([CH:50]([OH:51])[CH2:49][CH2:48][O:47][CH2:46][CH2:45][O:44][CH2:43][CH2:42][O:41][CH2:40][CH2:39][O:38][CH2:37][CH2:36][NH2:35])=[O:34])[CH2:19][CH2:20]2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1]

参加物

3

反応物 2

HCID 21121691HCID 21121691、化合物HCID 22731902Amino-PEG4-acid

生成物 1

HCID 131736276[4-(Cholest-5-en-3beta-yloxy)butanoyl]-15-amino-4,7,10,13-tetraoxapentadecanol収率 155.1%

実験手順

The mixture of pentafluorophenyl ester of 4-(Cholest-5-en-3β-yloxy)butanoic acid (121 mg, 0.19 mmol) and 15-amino-4,7,10,13-tetraoxapentadecanoic acid (104 mg, 0.39 mmol) was dried in an apparatus equipped with septum for 4 h at room temperature and 0.1 Pa. The apparatus was flushed with argon (2×) and then dry N,N-dimethylformamide (4 ml) and N-ethyldiisopropylamine (1 ml) were added through the septum and the mixture was stirred at room temperature for 16 h. Flash chromatography of the crude reaction mixture on silica gel column (100 ml) in toluene-ethyl acetate (gradient: 0-40% ethyl acetate, 10 ml/min, 160 min) gave [4-(Cholest-5-en-3β-yloxy)butanoyl]-15-amino-4,7,10,13-tetraoxapentadecanol acid (general formula X, where n3=3 and n4=3; 208 mg, 88%). 1H NMR (400 MHz, Acetone) δ ppm: 3.71 t, J=6.32 Hz, 2H (CH2-3); 3.55-3.60 m, 14H (7×CH2—O); 3.51 t, J=5.60 Hz, 2H (CH2-14); 3.45 t, J=6.32 Hz, 2H (CH2-4′); 3.34 q, J=5.73 Hz, 1H (CH-3″); 2.53 t, J=6.32 Hz, 2H (CH2-2); 2.34 ddd, J=13.20, 4.70, 2.10 Hz, 1H (H-4a″); 2.24 t, J=7.45 Hz, 2H (CH2-2′); 1.82-2.17 m, 5H (cholesteryl); 1.76-1.82 m, 2H (CH2-3′); 1.01 s, 3H (CH3-19″); 0.94 d, J=6.57 Hz, 3H (CH3-21″); 0.87 d, J=1.26 Hz, 3H (CH3-26″); 0.86 d, J=1.52 Hz, 3H (CH3-27″); 0.81-1.66 m, 34H (cholesteryl); 0.71 s, 3H (CH3-18″); for C42H73NO8—H HR-MS, calculated m/z: 720.5409. found m/z: 720.5407.

後処理

  1. customwas dried in an apparatus
  2. customequipped with septum for 4 h at room temperature
  3. customThe apparatus was flushed with argon (2×)
  4. additiondry N,N-dimethylformamide (4 ml) and N-ethyldiisopropylamine (1 ml) were added through the septum
  5. customFlash chromatography of the crude reaction mixture on silica gel column (100 ml) in toluene-ethyl acetate (gradient: 0-40% ethyl acetate, 10 ml/min, 160 min)

出典と根拠

ORDレコード
ord-eb1fd173f68645658c080fc933930cd1
出典データセット
uspto-grants-2016_07
特許番号
US09393200B2

反応ノート

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