Hydrochloric Acid → N-(5-hydroxymethyl-2-methoxyphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamide

HRID 537621ノート

反応式

HRID 537621 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](OC)=[O:10])=[CH:5][C:4]=1[NH:13][C:14]([CH:16]1[CH2:21][CH:20]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH:19]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[CH:18]([O:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH3:78])[CH2:17]1)=[O:15].CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.Cl>C1COCC1>[OH:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([NH:13][C:14]([CH:16]2[CH2:17][CH:18]([O:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH3:78])[CH:19]([O:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH3:59])[CH:20]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:21]2)=[O:15])[CH:5]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 87324411N-(2-methoxy-5-methoxycarbonylphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamideHCID 131729488DIBAL toluene

生成物 1

HCID 53257320N-(5-hydroxymethyl-2-methoxyphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamide収率 86%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

N-(2-Methoxy-5-methoxycarbonylphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamide (225 mg, 0.21 mmol) was dissolved in dehydrated THF (2.5 ml), 1M DIBAL/toluene (0.6 ml, 0.6 eq) was added dropwise, and the mixture was stirred for 5 hr. After completion of the reaction, 1N hydrochloric acid was added to quench the reaction, and the mixture was extracted with chloroform (10 ml), and washed with 1N hydrochloric acid (5 ml). The solvent was evaporated and the residue was precipitated with methanol (15 ml) and slurry-washed with acetonitrile (10 ml) and 1N hydrochloric acid (10 ml) to give N-(5-hydroxymethyl-2-methoxyphenyl) 3,4,5-tris(octadecyloxy)cyclohexylcarboxamide (200 mg, 0.18 mmol, yield 86%).

後処理

  1. additionwas added
  2. customto quench
  3. customthe reaction
  4. extractionthe mixture was extracted with chloroform (10 ml)
  5. washwashed with 1N hydrochloric acid (5 ml)
  6. customThe solvent was evaporated
  7. customthe residue was precipitated with methanol (15 ml)
  8. washslurry-washed with acetonitrile (10 ml) and 1N hydrochloric acid (10 ml)

出典と根拠

ORDレコード
ord-83125a43fae3432780529882ae883b44
出典データセット
uspto-grants-2014_10
特許番号
US08859732B2

反応ノート

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