Sodium Acetate → HCID 66649696, compound

HRID 420319Notes

Reaction equation

HRID 420319 reaction equation
Cl.[NH2:2][C@@H:3]1[C@@H:8]([OH:9])[C@H:7]([CH2:10][C:11]2[CH:16]=[C:15]([O:17][C@@:18]([CH3:25])(OC)[C:19]([F:22])([F:21])[F:20])[C:14]([N+:26]([O-:28])=[O:27])=[C:13]([F:29])[CH:12]=2)[CH2:6][S:5][CH2:4]1.C[C:31]([O-:33])=O.[Na+].[C:35]([C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][CH:46]=1)[CH:42]=O)([CH3:38])([CH3:37])[CH3:36].[BH3-]C#N.[Na+]>CO.C(Cl)Cl.C(O)(=O)C>[C:35]([C:39]1[CH:40]=[C:41]([CH:44]=[CH:45][CH:46]=1)[CH2:42][NH:2][C@@H:3]1[C@@H:8]([OH:9])[C@H:7]([CH2:10][C:11]2[CH:16]=[C:15]([O:17][C@H:18]([CH2:25][O:33][CH3:31])[C:19]([F:22])([F:20])[F:21])[C:14]([N+:26]([O-:28])=[O:27])=[C:13]([F:29])[CH:12]=2)[CH2:6][S:5][CH2:4]1)([CH3:38])([CH3:36])[CH3:37]

Participants

7

Reactant 4

HCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 101925883-tert-butylbenzaldehydeHCID 66649592HCID 66649592, compound

Product 1

HCID 66649696HCID 66649696, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (3R,4S,5S)-3-amino-5-[3-fluoro-4-nitro-5-((R)-2,2,2-trifluoro-1-methoxy-methyl-ethoxy)-benzyl]-tetrahydro-thiopyran-4-ol hydrochloride (1.217 g, 2.52 mmol) in MeOH-CH2Cl2 1:2 (28 mL) was added NaOAc (0.517 g, 6.3 mmol), powdered molecular sieves (4A) and 3-tert-butyl-benzaldehyde (CAS registry 23039-28-3) (0.413 g, 2.55 mmol). The reaction mixture was stirred at 25° C. for 16 h, acetic acid (0.5 mL) was added followed by NaBH3CN (0.396 g, 6.3 mmol). The reaction mixture was stirred at room temperature for 3 h and was quenched by adding 2N aq. HCl solution. EtOAc was added and the solution was washed with 2N K2CO3 solution and with brine. The organic phase was dried over Na2SO4, filtered and evaporated. The title compound was obtained after purification by flash-chromatography on NH4OH deactivated silica gel (90 g, toluene-EtOAc 1:1) as a light yellow oil: TLC (toluene-ETA 85:15) Rf=0.52; HPLC RtA=2.178 min; ESIMS [M+H]+=575; 1H NMR (600 MHz, CDCl3): δ 7.33 (s, 1H), 7.28 (s, 1H), 7.26 (m, 2H), 7.18-7.08 (m, 2H), 5.7 (broad, 1H), 5.06 (d, 1H), 3.9-3.78 (m, 2H), 3.71-3.62 (m, 2H), 3.31 (s, 3H), 3.22 (d, 1H), 2.90 (m, 1H), 2.82 (d, 1H), 2.55 (m, 1H), 2.48 (s broad, 1H), 2.41 (m, 1H), 2.35-2.20 (m, 3H), 1.93 (m, 1H), 1.25 (s, 9H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 h
  2. customwas quenched
  3. additionby adding 2N aq. HCl solution
  4. additionEtOAc was added
  5. washthe solution was washed with 2N K2CO3 solution and with brine
  6. dry with materialThe organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-23c60799a5674907b7f175a4b3d8245d
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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