Acetonitrile → HCID 72524391、化合物

HRID 1991026ノート

反応式

HRID 1991026 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 Reference Production Example 1 (44 mg, 0.037 mmol) and acetonitrile (0.88 ml), 46-48% aqueous hydrogen fluoride (HF) (0.12 ml) was gently added, and this was followed by overnight stirring at room temperature. The reaction product was poured over an ethyl acetate-water mixed solution and extracted. The organic phase obtained was washed with water and saline, and dried over magnesium sulfate (MgSO4). After the MgSO4 was separated by filtration, the filtrate was concentrated under reduced pressure. 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 materialdried over magnesium sulfate (MgSO4)
  6. customAfter the MgSO4 was separated by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified

出典と根拠

ORDレコード
ord-bc6f0cc424c6470c8937ee6a899a76ed
出典データセット
uspto-grants-2010_01
特許番号
US07645614B2

反応ノート

読み込み中…