Tributylphosphine → HCID 23157548, compound

HRID 508074Notes

Reaction equation

HRID 508074 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][S:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20]O)[CH:15]=2)=[C:9]([CH3:22])[CH:8]=1)[CH3:2].[F:23][C:24]1[CH:29]=[C:28]([NH:30][S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[N+:40]([O-:42])=[O:41])(=[O:33])=[O:32])[CH:27]=[CH:26][C:25]=1[CH2:43][CH2:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH2:1]([O:3][CH2:4][CH2:5][S:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:30]([S:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[N+:40]([O-:42])=[O:41])(=[O:32])=[O:33])[C:28]3[CH:27]=[CH:26][C:25]([CH2:43][CH2:44][C:45]([O:47][C:48]([CH3:51])([CH3:49])[CH3:50])=[O:46])=[C:24]([F:23])[CH:29]=3)[CH:15]=2)=[C:9]([CH3:22])[CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 23157458HCID 23157458, compoundHCID 23157566HCID 23157566, compound

Product 1

HCID 23157548HCID 23157548, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {4′-[(2-ethoxyethyl)thio]-2′,6′-dimethylbiphenyl-3-yl}methanol (0.94 g, 2.98 mmol), tert-butyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (1.13 g, 3.13 mmol) and tributylphosphine (1.03 mL, 3.87 mmol) in tetrahydrofuran (25 mL) was added 1,1′-(azodicarbonyl)dipiperidine (1.01 g, 3.87 mmol) under stirring at room temperature, and the mixture was stirred for 3 days. The resulting precipitate was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane/ethyl acetate=5/1-hexane/ethyl acetate=3/1) to give a mixture (1.96 g) of tert-butyl 3-(4-{({4′-[(2-ethoxyethyl)thio]-2′,6′-dimethylbiphenyl-3-yl}methyl)[(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate, {4′-[(2-ethoxyethyl)thio]-2′,6′-dimethylbiphenyl-3-yl}methanol and tert-butyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate as a yellow oil. In the same manner as in Example 144, the title compound (1.25 g, yield 55%, 2 steps) was obtained as a colorless amorphous powder from the above-mentioned mixture (1.96 g).

Workup

  1. stirringthe mixture was stirred for 3 days
  2. filtrationThe resulting precipitate was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a3199d31487341b59208f15fd147e494
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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