Methanol → HCID 11239597, compound

HRID 1174379Notes

Reaction equation

HRID 1174379 reaction equation
[CH3:1][O:2][C:3](=[O:50])[NH:4][C@@H:5]([CH2:47]SC)[C:6](=[O:46])[NH:7][C@@H:8]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C@@H:9]([OH:38])[CH2:10][C@H:11]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[CH:28][CH:27]=1)[NH:12][C:13](=[O:24])[C@H:14]([C:20]([CH3:23])([CH3:22])[CH3:21])[NH:15][C:16](=[O:19])[O:17][CH3:18].O[O:52][S:53]([O-:55])=O.[K+].[CH3:57]O>O>[CH3:1][O:2][C:3](=[O:50])[NH:4][C@@H:5]([CH2:47][S:53]([CH3:57])(=[O:55])=[O:52])[C:6](=[O:46])[NH:7][C@@H:8]([CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[C@@H:9]([OH:38])[CH2:10][C@H:11]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=2)=[CH:28][CH:27]=1)[NH:12][C:13](=[O:24])[C@H:14]([C:20]([CH3:23])([CH3:22])[CH3:21])[NH:15][C:16](=[O:19])[O:17][CH3:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 69779586HCID 69779586, compound

Product 1

HCID 11239597HCID 11239597, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of Example 153B (20 mg, 0.028 mmol) in methanol (0.28 mL) and water (0.28 mL) was treated with oxone (52 mg, 0.082 mmol) at 25° C. for 1 h. The solvents were evaporated, and the residue was partitioned between ethyl acetate/water, the organic layer was separated, washed with brine, dried over MgSO4, filtered, and the solvents were evaporated. The crude residue was purified by silica gel chromatography eluting with a gradient of dichloromethane, 100% ethyl acetate, to 95% ethyl acetate/5% methanol to give the title compound (9 mg, 43%). 1H NMR (300 MHz, MeOH-D6) δ ppm 0.86(s, 9H), 1.69-1.60(m, 2H), 2.70-2.63(m, 1H), 2.89-2.82(m, 3H), 2.93(s, 3H), 3.3-3.23(m, 1H), 3.45-3.39(m, 1H), 3.53(s, 3H), 3.67(s, 3H), 3.77-3.73(t, J=6.62 Hz, 1H), 3.81(s, 1H), 4.27-4.22(m, 1H), 4.33(m, 1H), 4.63-4.59(dd, J=8.09, 4.78 Hz, 1H), 7.19-7.12(m, 1H), 7.24-7.23(d, J=4.41 Hz, 4H), 7.30-7.27(d, J=8.09 Hz, 2H), 7.35-7.30(m, 1H), 7.80-7.78(d, J=8.09 Hz, 2H), 7.82(m, 1H), 7.87-7.84(dd, J=6.99, 1.84 Hz, 1H), 8.58-8.57(d, J=4.04 Hz, 1H).

Workup

  1. customThe solvents were evaporated
  2. customthe residue was partitioned between ethyl acetate/water
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were evaporated
  8. customThe crude residue was purified by silica gel chromatography
  9. washeluting with a gradient of dichloromethane, 100% ethyl acetate, to 95% ethyl acetate/5% methanol

Sources & evidence

ORD record
ord-c186299ea37747c99aa23b99b2dd1ce3
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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