Acetonitrile → HCID 72524391、化合物

HRID 734178ノート

反応式

HRID 734178 の反応式
[CH2:1]([CH:4]1[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]([OH:39])([CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])[C:19](=[O:40])[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11](=[O:42])[O:10][CH:9]([C:43]([CH3:72])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([O:51][C:52](=[O:69])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][C:59]([O:61][Si](C(C)(C)C)(C)C)=[O:60])[CH:47]([O:70][CH3:71])[CH2:46]2)[CH:8]([CH3:73])[CH:7]([O:74][Si](C(C)(C)C)(C)C)[CH2:6][C:5]1=[O:82])[CH:2]=[CH2:3].C(#N)C.F>C(OCC)(=O)C.O>[CH2:1]([CH:4]1[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]([OH:39])([CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])[C:19](=[O:40])[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11](=[O:42])[O:10][CH:9]([C:43]([CH3:72])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([O:51][C:52](=[O:69])[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][C:59]([OH:61])=[O:60])[CH:47]([O:70][CH3:71])[CH2:46]2)[CH:8]([CH3:73])[CH:7]([OH:74])[CH2:6][C:5]1=[O:82])[CH:2]=[CH2:3]

参加物

5

反応物 3

HCID 6342AcetonitrileHCID 14917Hydrofluoric AcidHCID 8660279117-Allyl-14-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-12-{2-[4-(7-(tert-butyl-dimethyl-silanyloxy-carbonyl)heptanoyl-oxy)-3-methoxy-cyclohexyl]-1-methyl-vinyl}-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9] octacos-18-ene-2,3,10,16-tetraone

生成物 1

HCID 72524391HCID 72524391、化合物収率 40%

試薬・触媒・溶媒 1

HCID 22728543Water ethylacetate溶媒

実験手順

To a mixture of the 17-allyl-14-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-12-{2-[4-(7-(tert-butyl-dimethyl-silanyloxy-carbonyl)heptanoyl-oxy)-3-methoxy-cyclohexyl]-1-methyl-vinyl}-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone prepared in Production Example 1 (44 mg, 0.037 mmol) and acetonitrile (0.88 ml), 46 to 48% aqueous hydrogen fluoride (HF) (0.12 ml) was gently added; this was followed by overnight stirring at room temperature. The reaction product was poured over an ethyl acetate-water mixed liquid and extracted. The organic phase obtained was washed with water and saline, after which it was dried with magnesium sulfate (MgSO4). After the MgSO4 was separated by filtration, concentration under reduced pressure was conducted. The residue thus obtained was purified using a silica gel column (5% methanol (in chloroform)) to yield the desired 17-allyl-1,14-di-hydroxy-12-{2-[4-(7-carboxy-heptanoyl-oxy)-3-methoxy-cyclohexyl]-1-methyl-vinyl}-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone (14.2 mg, 40%).

後処理

  1. additionwas gently added
  2. extractionextracted
  3. customThe organic phase obtained
  4. washwas washed with water and saline
  5. dry with materialafter which it was dried with magnesium sulfate (MgSO4)
  6. customAfter the MgSO4 was separated by filtration, concentration under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified

出典と根拠

ORDレコード
ord-ae9340a64a0447c6a9b7235667aaec75
出典データセット
uspto-grants-2009_09
特許番号
US07592187B2

反応ノート

読み込み中…