Triphenylphosphine → HCID 59373762, compound

HRID 1678723Notes

Reaction equation

HRID 1678723 reaction equation
[CH2:1]([N:8]([CH2:38][CH2:39][OH:40])[CH2:9][C@@H:10]([C:19]1[CH:20]=[CH:21][C:22]([Cl:37])=[C:23]([N:25]([S:33]([CH3:36])(=[O:35])=[O:34])[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:24]=1)[O:11][Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:41]1([CH3:47])C=CC=C[CH:42]=1.C(N(CCO)C[C@@H]([C:66]1[CH:67]=[CH:68][C:69](Cl)=[C:70]([N:72](S(C)(=O)=O)[C:73](=[O:79])[O:74][C:75]([CH3:78])([CH3:77])[CH3:76])[CH:71]=1)O[Si](CC)(CC)CC)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C[N:108](C(/N=N/C(N(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH2:1]([N:8]([CH2:9][C@@H:10]([C:19]1[CH:20]=[CH:21][C:22]([Cl:37])=[C:23]([N:25]([C:26]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:32])[S:33]([CH3:36])(=[O:34])=[O:35])[CH:24]=1)[O:11][Si:12]([CH2:15][CH3:16])([CH2:13][CH3:14])[CH2:17][CH3:18])[CH2:38][CH2:39][O:40][C:66]1[CH:71]=[C:70]2[C:69]([C:42]([CH2:41][CH3:47])=[N:108][N:72]2[C:73]([O:74][C:75]([CH3:76])([CH3:77])[CH3:78])=[O:79])=[CH:68][CH:67]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5353800DiamideHCID 59370765HCID 59370765, compoundHCID 67330214HCID 67330214, compound

Product 1

HCID 59373762HCID 59373762, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Tert-butyl 3-ethyl-6-hydroxyindazole-1-carboxylate (27.9 mg) that can be produced by the method described in Reference Example 14 or the like, and a (R)-tert-butyl 5-(2-(benzyl(2-hydroxyethyl)amino)-1-(triethylsilyloxy)ethyl)-2-chlorophenyl(methylsulfonyl)carbamate-toluene solution [0.5 mL; solution prepared by dissolving (R)-tert-butyl 5-(2-(benzyl(2-hydroxyethyl)amino)-1-(triethylsilyloxy)ethyl)-2-chlorophenyl(methylsulfonyl)carbamate (1.5265 g) that can be produced by the method described in Reference Example 75 or the like in dehydrated toluene (10 mL)] were dissolved in dehydrated toluene (0.5 mL), and triphenylphosphine (54.9 mg; manufactured by Wako Pure Chemical Industries, Ltd.) and TMAD (41.4 mg; manufactured by Masuda Chemical Industries, Co., Ltd.) were added to the solution. The mixture was stirred for 3 days at room temperature. The reaction solution was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=85:15→64:36), and thus the title compound (85.6 mg) was obtained.

Workup

  1. customsolution prepared
  2. customcan be produced by the method
  3. customThe reaction solution was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=85:15→64:36)

Sources & evidence

ORD record
ord-2140ce4f59da4b55b5427189ae094db0
Source dataset
uspto-grants-2011_08
Patent number
US08008506B2

Reaction notes

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