Trimethyl orthoformate → HCID 68864404, compound

HRID 1725980Notes

Reaction equation

HRID 1725980 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH2:16][C:15](=[O:22])[C:14]=2[C:13]=1[C:23]([O:25][CH3:26])=[O:24])(=[O:10])=[O:9].[CH3:27]OC(OC)OC.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[CH2:18][CH2:17][CH:16]=[C:15]([O:22][CH3:27])[C:14]=2[C:13]=1[C:23]([O:25][CH3:26])=[O:24])(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 68866025HCID 68866025, compound

Product 1

HCID 68864404HCID 68864404, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of Example 458A (240 mg, 0.64 mmol), trimethylorthoformate (0.7 mL, 6.4 mmol) and pyridinium p-toluenesulfonate (80 mg, 0.32 mmol) in methanol (7 mL) was refluxed overnight, cooled to room temperature, and partitioned between diethyl ether and brine. The organic phase was dried (MgSO4), filtered, concentrated, and passed through a silica gel plug eluting with 30% acetone/hexanes to provide the desired product (210 mg, 83% yield). MS (ESI) m/e 390 (M−H)−, 1H NMR (300 MHz, DMSO-d6) δ 9.82 (s, 1H), 7.73-7.62 (m, 2H), 7.44 (m, 1H), 7.31 (t, 1H), 7.22 (d, 1H), 7.02 (d, 1H), 5.19 (t, 1H), 3.54 (s, 3H), 3.50 (s, 3H), 2.64 (t, 2H), 2.19 (m, 2H).

Workup

  1. custompartitioned between diethyl ether and brine
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washeluting with 30% acetone/hexanes

Sources & evidence

ORD record
ord-1974f5e6c5ce47ef912bc25275e68ec1
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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