Sodium Bicarbonate → HCID 86728262, compound

HRID 1776858Notes

Reaction equation

HRID 1776858 reaction equation
C(OC([NH:8][C@@H:9]([CH:58]([CH3:60])[CH3:59])[C:10]([O:12][CH2:13][CH:14]1[N:19]2[C:20]3[CH:21]=[CH:22][CH:23]=[C:24]([F:27])[C:25]=3[CH:26]=[C:18]2[C:17]2[N:28]=[C:29]([C:32]3[C:33]([N:52]([CH3:57])[S:53]([CH3:56])(=[O:55])=[O:54])=[CH:34][C:35]4[O:39][C:38]([C:40]5[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=5)=[C:37]([C:47](=[O:50])[NH:48][CH3:49])[C:36]=4[CH:51]=3)[CH:30]=[CH:31][C:16]=2[O:15]1)=[O:11])=O)(C)(C)C.C([O-])(O)=O.[Na+]>ClCCl.C(O)(C(F)(F)F)=O>[NH2:8][C@@H:9]([CH:58]([CH3:60])[CH3:59])[C:10]([O:12][CH2:13][C@H:14]1[N:19]2[C:20]3[CH:21]=[CH:22][CH:23]=[C:24]([F:27])[C:25]=3[CH:26]=[C:18]2[C:17]2[N:28]=[C:29]([C:32]3[C:33]([N:52]([CH3:57])[S:53]([CH3:56])(=[O:54])=[O:55])=[CH:34][C:35]4[O:39][C:38]([C:40]5[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=5)=[C:37]([C:47](=[O:50])[NH:48][CH3:49])[C:36]=4[CH:51]=3)[CH:30]=[CH:31][C:16]=2[O:15]1)=[O:11]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 86728260HCID 86728260, compound

Product 1

HCID 86728262HCID 86728262, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (2S)-(11-fluoro-2-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-6-yl)methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate (30 mg, 0.04 mmol) in dichloromethane (2 mL), TFA (0.5 mL) was added. The mixture was stirred at room temperature overnight. The mixture was poured into sat NaHCO3 solution (20 mL) and extracted with dichloromethane. The combined organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified using prep-TLC (dichloromethane:MeOH=40:1) to provide the product Compound 102 (25 mg, yield: 94%). 1H-NMR (CDCl3, 400 MHz) δ 8.03 (s, 1H), 7.95˜7.99 (m, 2H), 7.66 (s, 1H), 7.53 (d, J=8.4 Hz, 1H), 7.46 (d, J=8.4 Hz, 1H), 7.19˜7.25 (m, 5H), 6.84˜6.89 (m, 1H), 6.63˜6.66 (m, 1H), 5.95 (br s, 1H), 4.41˜4.47 (m, 1H), 4.32˜4.37 (m, 1H), 3.39 (s, 3H), 3.23 (d, J=5.2 Hz, 1H), 3.01 (d, J=4.8 Hz, 3H), 2.74 (s, 3H), 1.82˜1.91 (m, 1H), 0.91 (d, J=6.8 Hz, 3H), 0.81 (d, J=6.8 Hz, 3H). MS (M+H)+: 744.

Workup

  1. additionThe mixture was poured
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-8c84881d5cb544b1acc71fb174b53ab0
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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