Hydrochloric Acid → HCID 57386562, compound

HRID 420268Notes

Reaction equation

HRID 420268 reaction equation
Cl.[NH2:2][C@@H:3]1[C@@H:8]([OH:9])[C@H:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[C:13]([F:20])[CH:12]=2)[CH2:6][S:5](=[O:22])(=[O:21])[CH2:4]1.CC([O-])=O.[Na+].[C:28]([C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH:35]=O)([CH3:31])([CH3:30])[CH3:29].[BH3-]C#N.[Na+].Cl.C([O-])([O-])=O.[K+].[K+]>CO.C(Cl)Cl>[C:28]([C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35][NH:2][C@@H:3]1[C@@H:8]([OH:9])[C@H:7]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[C:13]([F:20])[CH:12]=2)[CH2:6][S:5](=[O:22])(=[O:21])[CH2:4]1)([CH3:31])([CH3:29])[CH3:30]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 101925883-tert-butylbenzaldehydeHCID 131729360HCID 131729360, compound

Product 1

HCID 57386562HCID 57386562, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of (3R*,4S*,5S*)-3-amino-5-(3-fluoro-4-nitro-benzyl)-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-4-ol hydrochloride (0.14 g, 0.39 mmol) in MeOH-CH2Cl2 1:1 (3 mL) was added NaOAc (0.065 g, 0.78 mmol) and 3-tert-butyl-benzaldehyde (0.07 g, 0.43 mmol). The reaction mixture was stirred at 25° C. for 0.5 h before NaBH3CN (0.039 g, 0.59 mmol) was added followed by stirring for 16 h. The reaction mixture was acidified with 1N aq. HCl, stirred for 15 min, basified with K2CO3-solution and extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and evaporated. The title compound was obtained after purification by flash-chromatography on silica gel (hexane-CH2Cl2-MeOH 20:20:1 to 1:20:5) as a light yellow foam: TLC (EtOAc) Rf=0.45; HPLC RtA=1.78 min; ESIMS [M+H]+=465; 1H NMR (400 MHz, CDCl3): δ 8.02 (t, 1H), 7.1-7.4 (m, 6H), 4.18 (s, 1H), 3.88 (d, 1H), 3.78 (d, 1H), 3.64 (m, 1H), 3.41 (ddd, 1H), 3.24 (ddd, 1H), 3.12 (dt, 1H), 3.00 (dd, 1H), 2.84, (m, 2H), 2.69 (m, 2H), 2.44 (m, 1H), 1.33 (s, 9H).

Workup

  1. additionwas added
  2. stirringstirred for 15 min
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-175a6f05e00d4d73b710c74cd49283eb
Source dataset
uspto-grants-2012_01
Patent number
US08093406B2

Reaction notes

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