Triacetoxyperiodinane → N-((4aS,5S,7aS)-7a-(2,3-difluorophenyl)-5-formyl-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide

HRID 707685Notes

Reaction equation

HRID 707685 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@:9]12[CH2:17][O:16][C@H:15]([CH2:18][OH:19])[C@H:14]1[CH2:13][S:12][C:11]([NH:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[N:10]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@:9]12[CH2:17][O:16][C@H:15]([CH:18]=[O:19])[C@H:14]1[CH2:13][S:12][C:11]([NH:20][C:21](=[O:28])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[N:10]2

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 68173766N-((4aS,5S,7aS)-7a-(2,3-difluorophenyl)-5-(hydroxymethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide

Product 1

HCID 86724397N-((4aS,5S,7aS)-7a-(2,3-difluorophenyl)-5-formyl-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

N-((4aS,5S,7aS)-7a-(2,3-difluorophenyl)-5-(hydroxymethyl)-4a,5,7,7a-tetrahydro-4H-furo[3,4-d][1,3]thiazin-2-yl)benzamide, obtained in preparation example 1-(6), (4.20 g) was dissolved in DCM (60 mL) and the solution was cooled to 0° C. 1,1,1-Tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one (5.50 g) was added portionwise over 10 min, and the reaction mixture was allowed to warm to RT. After stirring for 2 h, NaHCO3 (sat., aq., 100 mL) was added, and the mixture was extracted with DCM (3×150 mL). The combined organic portions were dried over MgSO4 and evaporated to afford the title compound (3.04 g, approx. purity 60%) which was used in the subsequent step without purification. 1H NMR (400 MHz, CDCl3) δ ppm 2.97 (dd, J=14.0, 4.2 Hz, 1H), 3.23 (d, J=11.6 Hz, 1H), 3.29-3.38 (m, 1H), 4.08-4.18 (m, 1H), 4.56-4.83 (m, 2H), 7.11-7.24 (m, 3H), 7.39-7.64 (m, 3H), 7.98-8.18 (m, 2H), 9.96 (d, J=1.0 Hz, 1H).

Workup

  1. temperatureto warm to RT
  2. extractionthe mixture was extracted with DCM (3×150 mL)
  3. dry with materialThe combined organic portions were dried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-cad4934bda064951a6c0cd89c1bdbbe7
Source dataset
uspto-grants-2015_11
Patent number
US09175013B2

Reaction notes

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