Hydrochloric Acid → HCID 67235300, compound

HRID 1748274Notes

Reaction equation

HRID 1748274 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[CH:5]=[C:4]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[CH3:22][C@@H:23]1OS(=O)(=O)[N:26]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:25][CH2:24]1.Cl>CN1C(=O)CCC1>[C:34]([O:33][C:31]([NH:26][CH2:25][CH2:24][C@H:23]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[CH:5]=[C:4]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:22])=[O:32])([CH3:37])([CH3:36])[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 44754779Diethyl 1H-indole-2,6-dicarboxylate2×HCID 86682389HCID 86682389, compound

Product 1

HCID 67235300HCID 67235300, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent3×

Procedure

A stirred suspension of 60% NaH (840 mg, 21 mmol) in NMP (40 mL) is cooled in an ice bath, and a solution of diethyl 1H-indole-2,6-dicarboxylate (Intermediate A, 5.8 g, 22 mmol) in NMP (20 mL) is added. The mixture is stirred for 20 min, then a solution of tert-butyl (6S)-6-methyl-1,2,3-oxathiazinane-3-carboxylate 2,2-dioxide (5.0 g, 20 mmol) in NMP (20 mL) is added. The reaction mixture is stirred for 30 min at 0° C. and is warmed to room temperature and stirred for 48 h. The reaction is poured into ice water and the resultant solid is isolated by filtration. The filtrate is acidified to pH 3 with 1N aqueous HCl and extracted with EtOAc. The combined extracts are washed with water 4 times, then brine, dried (Na2SO4) and concentrated to afford the title compound (6.0 g, crude) as an oil which was used in the next step without purification.

Workup

  1. temperatureis cooled in an ice bath
  2. stirringThe reaction mixture is stirred for 30 min at 0° C.
  3. stirringstirred for 48 h
  4. customthe resultant solid is isolated by filtration
  5. extractionextracted with EtOAc
  6. washThe combined extracts are washed with water 4 times
  7. dry with materialbrine, dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d27cfdc986a44fd3834d54c992acd55f
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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