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4-Methoxyphenylacetic Acid → HCID 58438501, compound

HRID 1913446
Notes
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Reaction equation

HRID 1913446 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.[CH2:13]1[C:16]2([CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:15][N:14]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([N:19]2[CH2:20][CH2:21][C:16]3([CH2:15][N:14]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:13]3)[CH2:17][CH2:18]2)=[O:12])=[CH:7][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 76904-Methoxyphenylacetic AcidHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23282935tert-Butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate

Product 1

HCID 58438501HCID 58438501, compound

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

To a solution of p-methoxyphenylacetic acid (1.26 g, 7.61 mmol) and tert-butyl 2,7-diazaspiro[3.5]nonane-2-carboxylate (2.00 g, 7.61 mmol) in dichloromethane (25 mL) was added triethylamine (2.12 mL, 15.2 mmol) and HATU (3.47 g, 9.12 mmol). The reaction was stirred for 15 hours. The reaction mixture was partitioned between dichloromethane and saturated sodium bicarbonate and the aqueous phase was washed with dichloromethane (2×20 mL). The combined organic layers were washed with water and brine, and dried over anhydrous MgSO4. Filtration and solvent removal afforded a crude product which was purified by silica chromatography on a Combiflash ISCO purification system (Teledyne Isco Inc., Lincoln, Nebr.), 100/0 to 50/50 heptanes/ethyl acetate gradient. The final product (I-1a) was obtained as clear oil which solidified upon standing at ambient temperature (2.75 g, 96%). MS (ES+) 375.4 (M+H)+. 1H NMR (CDCl3) δ 1.41 (s, 9H), 1.50 (br t, 2H), 1.65 (br t, 2H), 3.32 (br t, 2H), 3.52 (br t, 2H), 3.57-3.64 (m, 6H), 3.77 (s, 3H), 6.83 (d, 2H), 7.12 (d, 2H).

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and saturated sodium bicarbonate
  2. washthe aqueous phase was washed with dichloromethane (2×20 mL)
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationFiltration and solvent removal
  6. customafforded a crude product which
  7. customwas purified by silica chromatography on a Combiflash ISCO purification system (Teledyne Isco Inc., Lincoln, Nebr.), 100/0 to 50/50 heptanes/ethyl acetate gradient

Sources & evidence

ORD record
ord-5e85c5e79367475a947b969faa37722b
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08609680B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes