Triphenylphosphine → HCID 117713732, compound

HRID 1928617Notes

Reaction equation

HRID 1928617 reaction equation
[N:1]1[NH:2][N:3]=[C:4]([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([N:14]3[CH:18]=[N:17][N:16]=[N:15]3)=[N:12][CH:13]=2)[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:38][O:39][C:40]([C@H:42]1[CH2:47][C@@H:46](O)[CH2:45][CH2:44][N:43]1[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])=[O:41]>C1COCC1>[N:14]1([C:11]2[N:12]=[CH:13][C:8]([O:7][CH2:6][C:4]3[CH:5]=[N:1][N:2]([C@@H:46]4[CH2:45][CH2:44][N:43]([C:49]([O:51][C:52]([CH3:53])([CH3:54])[CH3:55])=[O:50])[C@@H:42]([C:40]([O:39][CH3:38])=[O:41])[CH2:47]4)[N:3]=3)=[CH:9][CH:10]=2)[CH:18]=[N:17][N:16]=[N:15]1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 2734504(2R,4S)-N-Boc-4-Hydroxypiperidine-2-Carboxylic Acid Methyl EsterHCID 577083825-((2H-1,2,3-Triazol-4-yl)methoxy)-2-(1H-tetrazol-1-yl)pyridine

Product 1

HCID 117713732HCID 117713732, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-((2H-1,2,3-triazol-4-yl)methoxy)-2-(1H-tetrazol-1-yl)pyridine (600 mg, 2.45 mmol), triphenylphosphine (1.5 eq.), and (2R,4S)-N-Boc-4-hydroxypiperidine-2-carboxylic acid methyl ester (1.5 eq.) dissolved in THF (20 mL) at 0° C. was added a solution of di-tertbutylazodicarboxylate (1.5 eq.) in THF (5 mL) drop wise. The reaction was allowed to warm to room temperature overnight and the solvents removed in vacuo The crude material was purified by flash column chromatography on silica gel to afford the desired product. 1H NMR (CDCl3): δ 9.44 (1H, s), 8.27 (1H, d), 8.03 (1H, d), 7.71 (1H, s), 7.58 (1H, dd), 5.27 (2H, s), 4.99-5.19 (1H, m), 4.57 (1H, m), 4.11-4.31 (1H, m), 3.79 (3H, s), 3.04-3.24 (1H, m), 2.75 (1H, m), 2.18-2.32 (2H, m), 2.05 (1H, m), 1.50 (9H, s). ES+-MS found: 486.1.

Workup

  1. customthe solvents removed in vacuo The crude material
  2. customwas purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-caf6a16b102149d0811e72dbaedc856c
Source dataset
uspto-grants-2012_05
Patent number
US08183381B2

Reaction notes

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