Toluene → HCID 178501030, compound

HRID 1417538Notes

Reaction equation

HRID 1417538 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:34][CH2:33][C@:7]2([O:11][CH2:10][C@H:9]([C:12]3[CH:17]=[C:16]([C:18]4[C:19]([CH3:30])=[N:20][N:21](C(OC(C)(C)C)=O)[CH:22]=4)[CH:15]=[CH:14][C:13]=3[O:31][CH3:32])[CH2:8]2)[C@@H:6]1[C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1)=[O:4].FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3]([C@H:5]1[CH2:34][CH2:33][C@:7]2([O:11][CH2:10][C@H:9]([C:12]3[CH:17]=[C:16]([C:18]4[C:19]([CH3:30])=[N:20][NH:21][CH:22]=4)[CH:15]=[CH:14][C:13]=3[O:31][CH3:32])[CH2:8]2)[C@@H:6]1[C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1)=[O:4]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 86753765HCID 86753765, compound

Product 1

HCID 178501030HCID 178501030, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (3S,5R,6S,7S)-6-(4-fluorophenyl)-3-(2-methoxy-5-(1-(tert-butoxycarbonyl)-3-methylpyrazol-4-yl)phenyl)-1-oxaspiro[4.4]nonane-7-carboxylic acid methyl ester (12 mg, 0.021 mmol) in 2.0 mL of dichloromethane was stirred at 0° C. and 2.0 mL of trifluoroacetic acid was added. After the solution had been stirred at 0° C. for 1.5 h, toluene (5 mL) was added and the solvent was evaporated at reduced pressure. The residue was purified by flash column chormatogrpahy on 1 g of silica gel, eluting with 25% ethyl acetate in dichloromethane to give 8 mg of colorless film (80% yield). 1H NMR (400 MHz, CDCl3): δ 7.60 (bs, 1H), 7.29 (dd, 2H, J=9, 6 Hz), 7.22 (dd, 1H, J=8, 2 Hz), 6.91 (d, 1H, J=8 Hz), 6.89 (t,,2H, J=9 Hz), 6.86 (d, 1H, J=2 Hz), 6.21 (t, 1H, J=2 Hz), 4.77 (dd, 1H, J=12, 2 Hz), 4.10 (dd, 1H, J=12, 2 Hz), 3.85 (s, 3H), 3.59 (s, 3H), 3.47 (dt, 1H, J=11, 8 Hz), 3.22 (d, 1H, J=11 Hz), 2.43-2.22 (m, 2H), 2.40 (s, 3H), 2.15-1.94 (m, 2H). Mass spectrum (NH3CI): m/e=436 M+1.

Workup

  1. customthe solvent was evaporated at reduced pressure
  2. customThe residue was purified by flash column chormatogrpahy on 1 g of silica gel
  3. washeluting with 25% ethyl acetate in dichloromethane
  4. customto give 8 mg of colorless film (80% yield)

Sources & evidence

ORD record
ord-c90d144c0d5b47dc887f33c1ed4439f1
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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