Water → HCID 178439651, compound

HRID 1717771Notes

Reaction equation

HRID 1717771 reaction equation
[N:1]([CH:4]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]2[N:33]=[N:34][NH:35][N:36]=2)[CH:27]=1)[C:5]1[CH:25]=[CH:24][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[C:13]([OH:20])[C:12]=2[CH2:21][CH2:22][CH3:23])=[CH:7][CH:6]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH:4]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]2[NH:36][N:35]=[N:34][N:33]=2)[CH:27]=1)[C:5]1[CH:25]=[CH:24][C:8]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[C:13]([OH:20])[C:12]=2[CH2:21][CH2:22][CH3:23])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 57884509HCID 57884509, compound

Product 1

HCID 178439651HCID 178439651, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-[4-(4-{azido-[3-(2H-tetrazol-5-yl)-phenyl]-methyl}-benzyloxy)-2-hydroxy-3-propyl-phenyl]-ethanone (340 mg, 0.703 mmol), triphenylphosphine (195 mg, 0.74 mmol), water (0.5 mL), and tetrahydrofuran (5 mL) is stirred at room temperature 48 hr. The mixture is filtered, the cake is washed with tetrahydrofuran (2 mL) and dried under vacuum to give the title compound 169 mg, 52%, as a white solid. 1H NMR (DMSO-d6) δ 12.86 (s, 1H), 8.9 (bs, 2H), 8.18 (s, 1H), 7.98 (d, 1H), 7.80 (d, 1H), 7.35-7.58 (m, 6H), 6.72 (d, 1H), 5.74 (s, 1H), 5.28 (s, 2H), 2.58-2.62 (m, 5H), 1.46-1.54 (m, 2H), 0.88 (t, 3H). LCMS M−1 456.

Workup

  1. filtrationThe mixture is filtered
  2. washthe cake is washed with tetrahydrofuran (2 mL)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-63f2659685724e068325536d5f5b1e5d
Source dataset
uspto-grants-2010_09
Patent number
US07803938B2

Reaction notes

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