HCID 22977785, compound → N-Pipecolyl-4-amino-5-benzyloxy-2-oxotetrahydrofuran

HRID 1711934Notes

Reaction equation

HRID 1711934 reaction equation
C(OC([N:8]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:9]1[C:10]([NH:12][CH:13]1[CH:17]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:16][C:15](=[O:26])[CH2:14]1)=[O:11])=O)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[NH:8]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:9]1[C:10]([NH:12][CH:13]1[CH:17]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[O:16][C:15](=[O:26])[CH2:14]1)=[O:11]

Participants

4

Reactant 1

HCID 22977785HCID 22977785, compound

Product 1

HCID 66756117N-Pipecolyl-4-amino-5-benzyloxy-2-oxotetrahydrofuranYield 84.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

N—(N-tert-Butoxycarbonylpipecolyl)-4-amino-5-benzyloxy-2-oxo-tetrahydrofuran (654 mg) was dissolved in 15 ml of 25% trifluoroacetic acid in dichloromethane and stirred at room temperature. The mixture was concentrated to give a gummy residue. The residue was dissolved in dichloromethane and washed with 10% sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to give 422 mg of the title compound as a beige solid. 1H NMR (500 MHz, CDCl3) δ 7.38 (m, 5H), 7.15 (d, 1H), 5.55 (d, 1H), 4.95-4.8 (m, 1H), 4.78 (m, 1H), 4.65 (d, 1H), 4.45 (m, 1H), 3.2 (m, 0.5H), 3.05 (m, 0.5H), 2.95 (m, 0.5H), 2.85 (m, 0.5H), 2.65 (m, 1H), 2.55-2.38 (m, 1H), 1.95 (m, 1H), 1.8 (m, 1H), 1.6 (m, 2H), 1.38 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. customto give a gummy residue
  3. washwashed with 10% sodium bicarbonate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ce7a9f2d166d42f996dd90f0beb4c0eb
Source dataset
uspto-grants-2010_09
Patent number
US07790713B2

Reaction notes

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