HCID 68941527, compound → HCID 25144469, compound

HRID 576250Notes

Reaction equation

HRID 576250 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:19]3[CH2:28][CH2:29][CH2:30][O:31][C:32]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=[CH:34][CH:33]=2)=[C:10]([CH3:42])[CH:9]=1)=[O:7])(C)(C)C>ClCCl.C(O)(C(F)(F)F)=O>[CH2:26]([O:25][C:23]([C:20]1[NH:21][C:22]2[C:18]([C:19]=1[CH2:28][CH2:29][CH2:30][O:31][C:32]1[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=3)[CH:35]=[CH:34][CH:33]=1)=[CH:17][CH:16]=[CH:15][C:14]=2[C:11]1[CH:12]=[CH:13][C:8]([C:6]([OH:7])=[O:5])=[CH:9][C:10]=1[CH3:42])=[O:24])[CH3:27]

Participants

4

Reactant 1

HCID 68941527HCID 68941527, compound

Product 1

HCID 25144469HCID 25144469, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of EXAMPLE 98C in dichoromethane (5 mL) and TFA (5 mL) was stirred at room temperature overnight and concentrated. The concentrate was partitioned between water (50 mL) and ethyl acetate (200 mL), and the organic phase was washed with brine and dried (Na2SO4), filtered and concentrated. 1H NMR (300 MHz, DMSO-d6) δ 12.88 (m, 1H), 11.00 (s, 1H), 8.22 (m, 1H), 7.85 (m, 3H), 7.86 (m, 1H), 7.73 (d, 1H), 7.32-7.55 (m, 5H), 7.08 (m, 2H), 6.92 (d, 1H), 4.25 (m, 4H), 3.36 (t, 2H), 2.24 (t, 2H), 2.10 (s, 3H), 1.26 (t, 3H).

Workup

  1. concentrationconcentrated
  2. customThe concentrate was partitioned between water (50 mL) and ethyl acetate (200 mL)
  3. washthe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4f249bd762984082a51b0703f338a4f2
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

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