Trifluoroacetic acid → HCID 71513400, compound

HRID 1914491Notes

Reaction equation

HRID 1914491 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C@@H:17]3[C@@H:21]([CH2:22][C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=4)[CH2:20][O:19][C:18]3=[O:33])=[CH:12][C:11]=2[O:34][CH3:35])=[O:8])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:4]1([C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C@@H:17]3[C@@H:21]([CH2:22][C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([O:31][CH3:32])[CH:24]=4)[CH2:20][O:19][C:18]3=[O:33])=[CH:12][C:11]=2[O:34][CH3:35])=[O:8])[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86676733HCID 86676733, compound

Product 1

HCID 71513400HCID 71513400, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-tert-butyl 4-(4-(((3R,4R)-4-(3,4-dimethoxybenzyl)-2-oxotetrahydrofuran-3-yl)methyl)-2-methoxyphenyl) piperazine-1,4-dicarboxylate (155 mg, 0.27 mmol, 1.0 eq) in DCM (5 mL) was added TFA (1 mL). The resulting mixture was stirred at rt for 3 h, concentrated, basified by sat. NaHCO3, and extracted with DCM (30 mL×3). The combined organic layers were dried over MgSO4, filtered and concentrated to afford 4-(((3R,4R)-4-(3,4-dimethoxybenzyl)-2-oxotetrahydrofuran-3-yl)methyl)-2-methoxyphenyl piperazine-1-carboxylate (76.5 mg, 59.5%). LRMS (M+H+) m/z calculated 485.2, found 484.9. 1H NMR (CDCl3, 400 MHz) δ 6.98 (d, 1H), 6.74-6.78 (m, 2H), 6.65-6.68 (m, 1H), 6.51-6.56 (m, 2H), 4.13-4.17 (m, 1H), 3.83-3.90 (m, 1H), 3.85 (s, 3H), 3.83 (s, 3H), 3.77 (s, 3H), 3.53-3.66 (m, 4H), 2.90-2.97 (m, 6H), 2.48-2.69 (m, 4H).

Workup

  1. concentrationconcentrated
  2. extractionextracted with DCM (30 mL×3)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8a24b933bbfd4e28a49bfd830ef77805
Source dataset
uspto-grants-2013_12
Patent number
US08614211B2

Reaction notes

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