Acetic Acid → HCID 178490616, compound

HRID 726674Notes

Reaction equation

HRID 726674 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@@H:15]([C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)[CH2:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C([Sn]([N:44]=[N+:45]=[N-:46])(CCCC)CCCC)CCC.C(O)(=O)C.[OH-].[Na+]>ClC1C=CC=CC=1Cl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C@@H:15]([C:23]3[CH:24]=[CH:25][C:26]([C:29]4[NH:46][N:45]=[N:44][N:30]=4)=[CH:27][CH:28]=3)[CH2:16][C:17]3[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 4984872Tributyltin azideHCID 22881398HCID 22881398, compound

Product 1

HCID 178490616HCID 178490616, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of (R)-4-[1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(4-pyridyl)ethyl]benzene-nitrile from Step 1 (350 mg, 0.88 mmol) and tributyltin azide (1.17 g, 3.5 mmol) in 1,2-dichlorobenzene (4 mL) was stirred at 150° C. for 2 hours. The reaction mixture was then cooled to room temperature and acetic acid (0.5 mL) was added. After 15 min, aqueous 1N NaOH was added and the aqueous phase was washed 3 times with ether. The aqueous phase was then treated with 25% aqueous NH4OAc and 6N HCl to pH 7 before it was extracted twice with CH2Cl2. The organic phase was then dried (MgSO4) and evaporated to afford the title compound as a yellow solid (341 mg, 88%). 1H NMR (400 MHz, CDCl3): d 1.55 (m, 2H), 1.80 (m, 6H), 3.30 (m, 1H), 3.45 (m, 1H), 3.80 (s, 3H), 4.20 (m, 1H), 4.70 (m, 1H), 6.70 (s, 1H), 6.80 (m, 2H), 7.00 (d, 2H), 7.20 (d, 2H), 7.90 (d, 2H), 8.40 (d, 2H).

Workup

  1. washthe aqueous phase was washed 3 times with ether
  2. additionThe aqueous phase was then treated with 25% aqueous NH4OAc and 6N HCl to pH 7 before it
  3. extractionwas extracted twice with CH2Cl2
  4. dry with materialThe organic phase was then dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-ae4912c83c6f49f9ba7a6e385fd99006
Source dataset
uspto-grants-1998_01
Patent number
US05710160

Reaction notes

Loading…