HCID 21949550, compound → HCID 21949526, compound

HRID 2215075Notes

Reaction equation

HRID 2215075 reaction equation
C(OC([O:8][CH2:9][CH:10]1[CH2:14][O:13][C:12](=[O:15])[N:11]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=O)(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[OH:8][CH2:9][CH:10]1[CH2:14][O:13][C:12](=[O:15])[N:11]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

4

Reactant 1

HCID 21949550HCID 21949550, compound

Product 1

HCID 21949526HCID 21949526, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-4 (446 mg) in a mixture of 10% TFA in dichloromethane (10 mL) was stirred at room temperature for 2 h and concentrated. The residue was purified by column chromatography. Eluting with 70–100% ethyl acetate in hexanes afforded the alcohol 1-5 (264 mg). 1H NMR (400 MHz, acetone-d6): δ 4.33 (t, 1H), 4.19 (t, 1H, OH), 4.14 (dd, 1H), 4.09 (q, 2H), 3.95 (m, 1H), 3.78 (m, 1H), 3.65 (m, 1H), 3.38 (m, 1H), 3.16 (m, 1H), 2.29 (t, 2H), 1.70–1.55 (m, 4H), 1.45–1.30 (m, 4H), 1.21 (t, 3H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography
  3. washEluting with 70–100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-348f7bcd81da40ccba9cb74c020591d5
Source dataset
uspto-grants-2006_09
Patent number
US07109223B2

Reaction notes

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