Acetonitrile → HCID 72524391, compound

HRID 2075624Notes

Reaction equation

HRID 2075624 reaction equation
[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]

Participants

5

Reactant 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

Product 1

HCID 72524391HCID 72524391, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

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), 46-48% 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 fluid and extracted. The organic phase obtained was washed with water and brine, 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%).

Workup

  1. additionwas gently added
  2. extractionextracted
  3. customThe organic phase obtained
  4. washwas washed with water and brine
  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

Sources & evidence

ORD record
ord-54a22d9f3ca64e38b4e96ad8e777b691
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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