Water → HCID 178462419, compound

HRID 1766904Notes

Reaction equation

HRID 1766904 reaction equation
[C:1]([O:55]CC=C)(=[O:54])[CH2:2][CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([O:16][C@:17]([C:46]1[CH:51]=[CH:50][C:49]([F:52])=[CH:48][C:47]=1[F:53])([CH2:40][N:41]1[CH:45]=[N:44][CH:43]=[N:42]1)[C@H:18]([S:20][C@@H:21]1[CH2:26][O:25][C@@H:24](/[CH:27]=[CH:28]/[CH:29]=[CH:30]/[C:31]2[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][C:32]=2[F:39])[O:23][CH2:22]1)[CH3:19])=[O:15])=[O:5].O.C([SnH](CCCC)CCCC)CCC.CCCCCC>ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([O:16][C@:17]([C:46]1[CH:51]=[CH:50][C:49]([F:52])=[CH:48][C:47]=1[F:53])([CH2:40][N:41]1[CH:45]=[N:44][CH:43]=[N:42]1)[C@H:18]([S:20][C@@H:21]1[CH2:26][O:25][C@@H:24](/[CH:27]=[CH:28]/[CH:29]=[CH:30]/[C:31]2[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][C:32]=2[F:39])[O:23][CH2:22]1)[CH3:19])=[O:15])(=[O:5])[CH2:3][CH2:2][C:1]([OH:55])=[O:54]

Participants

7

Reactant 4

HCID 962WaterHCID 5948TributylstannaneHCID 8058HexaneHCID 178459561HCID 178459561, compound

Product 1

HCID 178462419HCID 178462419, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Allyl 2-[[(1R,2R)-2-[[trans-2-[(1E,3E)-4-(4-cyano-2-fluorophenyl)-1,3-butadienyl]-1,3-dioxan-5-yl]thio]-1-(2,4-difluorophenyl)-1-[(1H-1,2,4-triazol-1-yl)methyl]propoxy]carbonyl]benzyl succinate (150 mg, 1.84×10-4 mol) obtained from Example 19-(2) and bis(triphenylphosphine)dichloropalladium (2 mg) were dissolved in dichloromethane (1.5 ml). To the mixture was added water (0.1 ml), and tributyltin hydride (80 mg, 2.7×10−4 mol) was slowly added thereto over a period of 5 minutes at room temperature. The resulting mixture was stirred at room temperature for 15 minutes further, and then hexane was added thereto. The liberated oily insoluble material was separated by removing the supernatant liquid slowly. The insoluble residue was further washed twice with hexane. The oily residue was subjected to chromatography on a silica gel (8 g) column (eluent; ethyl acetate), and then purified by recycle preparative HPLC [LC-908; Japan Analytical Industry Co., Ltd.; GPC column JAIGEL-1H (20 mm i.d.×600 mm) and JAIGEL-2H (20 mm i.d.×600 mm) connected in series for use; solvent, chloroform] to afford the title compound (123.9 mg, 87% yield) as a colorless amorphous solid.

Workup

  1. additionwas slowly added
  2. customThe liberated oily insoluble material was separated
  3. customby removing the supernatant liquid slowly
  4. washThe insoluble residue was further washed twice with hexane
  5. custompurified by recycle preparative HPLC [LC-908; Japan Analytical Industry Co., Ltd.; GPC column JAIGEL-1H (20 mm i.d.×600 mm) and JAIGEL-2H (20 mm i.d.×600 mm) connected in series for use; solvent, chloroform]

Sources & evidence

ORD record
ord-83ccb9b79a05487f9dbe6eea5d572599
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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