HCID 131733283, compound → HCID 131733282, compound

HRID 513362Notes

Reaction equation

HRID 513362 reaction equation
[Si]([O:8][CH2:9][C@@H:10]1[CH2:14][C:13](/[CH:15]=[CH:16]/[CH3:17])=[CH:12][N:11]1[C:18]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][Si:29]([CH:36]([CH3:38])[CH3:37])([CH:33]([CH3:35])[CH3:34])[CH:30]([CH3:32])[CH3:31])=[CH:22][C:21]=1[NH:39][C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][C:47]([NH:50][C:51](=[O:68])[C@@H:52]([NH:54][C:55](=[O:67])[C@@H:56]([NH:60][C:61](=[O:66])[O:62][CH2:63][CH:64]=[CH2:65])[CH:57]([CH3:59])[CH3:58])[CH3:53])=[CH:46][CH:45]=1)=[O:41])=[O:19])(C(C)(C)C)(C)C>C(O)(=O)C.CO.O1CCCC1.O.CCOC(C)=O>[OH:8][CH2:9][C@@H:10]1[CH2:14][C:13](/[CH:15]=[CH:16]/[CH3:17])=[CH:12][N:11]1[C:18]([C:20]1[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][Si:29]([CH:36]([CH3:37])[CH3:38])([CH:33]([CH3:34])[CH3:35])[CH:30]([CH3:32])[CH3:31])=[CH:22][C:21]=1[NH:39][C:40]([O:42][CH2:43][C:44]1[CH:49]=[CH:48][C:47]([NH:50][C:51](=[O:68])[C@@H:52]([NH:54][C:55](=[O:67])[C@@H:56]([NH:60][C:61](=[O:66])[O:62][CH2:63][CH:64]=[CH2:65])[CH:57]([CH3:58])[CH3:59])[CH3:53])=[CH:46][CH:45]=1)=[O:41])=[O:19]

Participants

4

Reactant 1

HCID 131733283HCID 131733283, compound

Product 1

HCID 131733282HCID 131733282, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21657042HCID 21657042, compoundSolvent

Procedure

The silyl ether 14 (1.49 g, 1.52 mmol, 1.0 eq) was dissolved in a 7:1:1:2 mixture of acetic acid/methanol/tetrahydrofuran/water (14:2:2:4 mL) and allowed to stir at room temperature. After 2 hours the reaction was diluted with EtOAc (100 mL), washed sequentially with water, aq. sodium bicarbonate then brine. The organic phase was then dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 100/0 then 99/1 to 92/8 v/v DCM/MeOH) to afford the product as an orange solid (1.2 g, 92%). LC/MS (3.649 min (ES+)), m/z: 865.44 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.44 (s, 1H), 8.35 (s, 1H), 7.69 (br s, 1H), 7.53 (d, 2H, J=8.7 Hz), 7.32 (d, 2H, J=8.3 Hz), 6.78 (s, 1H), 6.56 (m, 2H), 6.32 (br s, 1H), 6.05 (d, 1H, J=14.9 Hz), 5.90 (m, 1H), 5.56 (m, 1H), 5.30 (m, 2H), 5.22 (m, 1H), 5.10 (d, 2H, J=3.1 Hz), 4.73 (m, 1H), 4.64 (m, 1H), 4.57 (d, 2H, J=5.8 Hz), 4.01 (m, 1H), 3.79 (m, 2H), 3.76 (s, 3H), 2.98 (dd, 1H, J=16.3, 10.2 Hz), 2.38 (dd, 1H, J=16.6, 4.1 Hz), 2.16 (m, 1H), 1.78 (dd, 3H, J=6.8, 0.9 Hz), 1.46 (d, 3H, J=7.1 Hz), 1.29 (m, 3H), 1.11 (d, 18H, J=7.4 Hz), 0.97 (d, 3H, J=6.7 Hz), 0.92 (d, 3H, J=6.8 Hz).

Workup

  1. washwashed sequentially with water, aq. sodium bicarbonate
  2. dry with materialThe organic phase was then dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (silica gel, 100/0

Sources & evidence

ORD record
ord-cb7768ebfa91496aa977b3521e40535f
Source dataset
uspto-grants-2015_08
Patent number
US09102704B2

Reaction notes

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