Triphenylphosphine → benzyl 2'-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-methylpropyl]oxy}-3-fluorobiphenyl-4-carboxylate

HRID 1026563Notes

Reaction equation

HRID 1026563 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[OH:24])[CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].[Si:25]([O:42][CH2:43][CH2:44][C@@H:45](O)[CH3:46])([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>O1CCCC1>[Si:25]([O:42][CH2:43][CH2:44][C@H:45]([O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[C:2]([F:1])[CH:3]=1)[CH3:46])([C:38]([CH3:39])([CH3:40])[CH3:41])([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 58005224(2S)-4-{[tert-butyl(diphenyl)silyl]oxy}butan-2-olHCID 68005717Benzyl 3-fluoro-2'-hydroxybiphenyl-4-carboxylate

Product 1

HCID 68006532benzyl 2'-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-methylpropyl]oxy}-3-fluorobiphenyl-4-carboxylateYield 118.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution (24 ml) of benzyl 3-fluoro-2′-hydroxybiphenyl-4-carboxylate (Example 1-3) (968 mg) were added at room temperature (2S)-4-{[tert-butyl(diphenyl)silyl]oxy}butan-2-ol (1.48 g), triphenylphosphine (1.18 g) and di-tert-butyl azodicarboxylate (1.04 g), followed by stirring overnight. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to afford benzyl 2′-{[(1R)-3-{[tert-butyl(diphenyl)silyl]oxy}-1-methylpropyl]oxy}-3-fluorobiphenyl-4-carboxylate (2.25 g).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c1dd8895e6a146e1a21136366cdb6e70
Source dataset
uspto-grants-2014_05
Patent number
US08729095B2

Reaction notes

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