Acetonitrile → HCID 72524391, 화합물

HRID 1991026노트

반응식

HRID 1991026 반응식
[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]

참가 물질

5

반응물 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

생성물 1

HCID 72524391HCID 72524391, 화합물수율 40%

시약·촉매·용매 1

HCID 22728543Water ethylacetate용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-bc6f0cc424c6470c8937ee6a899a76ed
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645614B2

반응 노트

불러오는 중…