Hydrochloric Acid → HCID 135955883, compound

HRID 731242Notes

Reaction equation

HRID 731242 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C@@H:6]1[N:13]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=1)[C:14](=[O:33])[CH2:15][C:16]1[NH:21][C:20]2[CH:22]=[CH:23][C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][C:19]=2[S:18](=[O:32])(=[O:31])[N:17]=1)=O.[O-]CC.[Na+].Cl>C(O)C>[F:41][C:38]1[CH:39]=[CH:40][C:35]([CH2:34][N:13]2[C:14](=[O:33])[C:15]([C:16]3[NH:21][C:20]4[CH:22]=[CH:23][C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][C:19]=4[S:18](=[O:32])(=[O:31])[N:17]=3)=[C:3]([OH:2])[CH:5]3[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:6]23)=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 69061039HCID 69061039, compound

Product 1

HCID 135955883HCID 135955883, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

cis-2-{(4-Fluoro-benzyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-amino}-cyclooctanecarboxylic acid methyl ester (0.241 g, 0.396 mmol) was dissolved in ethanol (4 mL), a 21% w/w solution of sodium ethoxide in ethanol (0.739 mL, 1.98 mmol) was added. The mixture was stirred at 60° C. for 4 h and allowed to cool to 25° C. The mixture was poured into a 0.5 M aqueous hydrochloric acid solution (100 mL). The product started to precipitate and was collected by vacuum filtration. The precipitate was washed with water and dried under high vacuum to afford the pure product N-{3-[1-(4-fluoro-benzyl)-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,9,10,10a-decahydro-cycloocta[b]pyridin-3-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide (0.07 g, 0.121 mmol, 31%), as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ: 1.24-1.83 (12H, m), 3.04 (3H, s), 3.73-3.58 (2H, m), 4.21-4.46 (1H, m),4.99 (1H, d, J=16 Hz), 7.18 (2H, t, J=8 Hz), 7.47-7.53 (6H, m), 10.08 (1H, s). LC-MS (ESI) calcd for C26H29FN4O6S2 576.15, found 577.5 [M+H+].

Workup

  1. temperatureto cool to 25° C
  2. customto precipitate
  3. filtrationwas collected by vacuum filtration
  4. washThe precipitate was washed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-b055c7c469b748619b09e1402e596782
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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