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

HRID 537621노트

반응식

HRID 537621 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-83125a43fae3432780529882ae883b44
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859732B2

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