Sodium Hydroxide → HCID 68175019, compound

HRID 707720Notes

Reaction equation

HRID 707720 reaction equation
O.O.[Sn](Cl)Cl.[F:6][C:7]1[C:12]([F:13])=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][C:8]=1[C@:17]12[CH2:25][O:24][C@H:23]([CH2:26][F:27])[C@H:22]1[CH2:21][S:20][C:19]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[N:18]2.[OH-].[Na+]>C(O)C>[NH2:14][C:10]1[CH:11]=[C:12]([F:13])[C:7]([F:6])=[C:8]([C@:17]23[CH2:25][O:24][C@H:23]([CH2:26][F:27])[C@H:22]2[CH2:21][S:20][C:19]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[N:18]3)[CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 86724407HCID 86724407, compound

Product 1

HCID 68175019HCID 68175019, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin(II) chloride dihydrate (2.06 g) was added to a suspension of tert-butyl ((4aS,5S,7aS)-7a-(2,3-difluoro-5-nitrophenyl)-5-(fluoromethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)carbamate, obtained in Preparation Example 2-(29), (1.17 g) in ethanol (20 ml) at RT. The mixture was stirred for 16 h at the same temperature (the solid gradually dissolved and the reaction color became yellow). The resultant mixture was poured into 2N sodium hydroxide solution and the organic was extracted with EtOAc. The organic layer was washed sequentially with water and brine, then dried over MgSO4. The solid was removed by filtration, and the filtrate was concentrated in vacuo. The crude mixture was purified by silica gel column chromatography (gradient from 20% to 60% EtOAc in heptane) acetate to afford the targeted compound (1.09 g) as a pale yellow solid. 1H-NMR (400 MHz, CDCl3) δ (ppm): 1.51 (s, 9H), 2.69-2.73 (m, 1H), 3.07-3.15 (m, 2H), 3.69 (bs, 2H), 3.84-3.85 (m, 1H), 4.49-4.67 (m, 4H), 6.34-6.36 (m, 1H), 6.44 (ddd, J=11.2, 6.4, 2.8 Hz, 1H)

Workup

  1. customat RT
  2. dissolutiongradually dissolved
  3. extractionthe organic was extracted with EtOAc
  4. washThe organic layer was washed sequentially with water and brine
  5. dry with materialdried over MgSO4
  6. customThe solid was removed by filtration
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe crude mixture was purified by silica gel column chromatography (gradient from 20% to 60% EtOAc in heptane) acetate

Sources & evidence

ORD record
ord-0045186341344ee1a50be2366c975c87
Source dataset
uspto-grants-2015_11
Patent number
US09175013B2

Reaction notes

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