Hydrochloric Acid → HCID 16244454, compound

HRID 2064752Notes

Reaction equation

HRID 2064752 reaction equation
B(F)(F)F.CCOCC.[CH3:10][O:11][C:12]([C:14]1[C:23]2[O:22][CH2:21][C:20](=O)[NH:19][C:18]=2[CH:17]=[CH:16][CH:15]=1)=[O:13].[BH4-].[Na+].Cl.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[CH3:10][O:11][C:12]([C:14]1[C:23]2[O:22][CH2:21][CH2:20][NH:19][C:18]=2[CH:17]=[CH:16][CH:15]=1)=[O:13]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 23770643Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate

Product 1

HCID 16244454HCID 16244454, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

Boron trifluoride diethyl etherate (10.1 mmol) is added dropwise to a mixture of 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid methyl ester (4.83 mmol) in THF (12 mL) to keep the temperature below 5° C. After 20 min NaBH4 (10.1 mmol) is added and the mixture is stirred at 5° C. for 60 min. EtOAc (6.0 mL) and hydrochloric acid (1.0 M, 6.0 mL) are added dropwise. The mixture is made basic by addition of sat. aq. NaHCO3 solution, the layers are separated and the aq. layer is extracted with EtOAc. The combined organic layers are dried over MgSO4 and concentrated in vacuo to give a crude product which is purified by CC (heptane to heptane/EtOAc 3/7). LC-MS: tR=0.69 min; [M+H]+=194.0.

Workup

  1. customthe temperature below 5° C
  2. customthe layers are separated
  3. extractionthe aq. layer is extracted with EtOAc
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-052ba936a60b4100a318775332611fa7
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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