Benzene → HCID 56620592, compound

HRID 1439876Notes

Reaction equation

HRID 1439876 reaction equation
C[C@H:2]1[CH2:33][C:32](C)=[CH:31][C@@H:30](CC=C)[C:28](=[O:29])[CH2:27][C@H:26](O)[C@@H:25](C)[C@@H:24](/[C:40](/C)=[CH:41]/[C@H:42]2[CH2:47][C@@H:46](OC)[C@H:45](O)[CH2:44][CH2:43]2)OC(=O)[C@H]2N(CCCC2)C(=O)C(=O)[C@]2(O)[O:10][C@@H:5]([C@@H:6](OC)C[C@H]2C)[C@@H:4]([O:56]C)[CH2:3]1.N(CCCC(OCC[Si](C)(C)C)=O)=C=[O:60].[CH:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1>C(N(CC)CC)C>[CH3:6][C:5](=[O:10])[C:4](=[O:56])[CH2:3][CH2:2][CH2:33][CH2:32][CH2:31][CH2:30][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:40][C:41](=[O:60])[CH2:42][CH:43]=[CH:44][CH2:45][CH2:46][CH2:47][CH2:73][CH2:78][CH2:77][CH2:76][CH2:75][CH3:74]

Participants

5

Reactant 3

HCID 241BenzeneHCID 445643TacrolimusHCID 184018732-Trimethylsilylethyl 4-isocyanatobutyrate

Product 1

HCID 56620592HCID 56620592, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineCatalyst

Procedure

A solution of the FR-900506 substance (310 mg), 2-trimethylsilylethyl 4-isocyanatobutyrate (350 mg) and triethylamine (6 drops) in anhydrous benzene (4 ml) was heated at 50° C. with stirring for 2 hours. The reaction mixture was allowed to stand at room temperature overnight. The mixture was concentrated to dryness under reduced processure to leave a residue, which was chromatographed on silica gel in chloroform. Elution was carried out with chloroform to give 17-allyl-12-[2-[3-methoxy-4-{3-(2-trimethylsilylethoxycarbonyl) propylcarbamoyloxy)cyclohexyl]-1-methylvinyl]-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11, 28-dioxa-4-azatricyclo[22.3.1.04,9 octacos-18-ene-2,3,10,16-tetraone (99 mg). This product was treated with tetra(n-butyl)ammonium fluoride (0.12 m mole) in tetrahydrofuran (2.5 ml) at room temperature for 20 minutes. The reaction mixture was concentrated to dryness under reduced pressure to leave a residue, which was purified with preparative thin layer chromatography on silica gel. Elution with a mixture of chloroform and methanol (5:1) gave 17-allyl-12-[2-{4-(3-carboxypropylcarbamoyloxy)-3-methoxycyclohexyl}-1-methylvinyl]-1, 14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (18.1 mg).

Workup

  1. waitto stand at room temperature overnight
  2. concentrationThe mixture was concentrated to dryness under reduced processure
  3. customto leave a residue, which
  4. customwas chromatographed on silica gel in chloroform
  5. washElution

Sources & evidence

ORD record
ord-34622e7889df490685e3b161ba1b9425
Source dataset
uspto-grants-1996_03
Patent number
US05496727

Reaction notes

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