(Diethylamino)sulfur trifluoride → HCID 117697539, compound

HRID 1778520Notes

Reaction equation

HRID 1778520 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:16]2[CH2:17][O:18][CH2:19][CH:9]1[C:10]1[CH:11]=[N:12][O:13][C:14]=1[CH:15]2O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:27])CC>C(Cl)Cl.CC(=O)OCC>[C:1]([O:5][C:6]([N:8]1[CH:16]2[CH2:17][O:18][CH2:19][CH:9]1[C:10]1[CH:11]=[N:12][O:13][C:14]=1[CH:15]2[F:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 117698123HCID 117698123, compound

Product 1

HCID 117697539HCID 117697539, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-Hydroxy-5,10-dioxa-4,12-diaza-tricyclo[6.3.1.0*2,6*]dodeca-2(6),3-diene-12-carboxylic acid tert-butyl ester 106d (141 mg, 0.5 mmol, 1.0 eq) in DCM (5 mL) was added DAST (166 mg, 1 mmol, 2.0 eq) at −78° C. Then mixture was stirred for 6 h from −78° C. to room temperature. The reaction was diluted with EA (20 mL), and washed with aqueous NaHCO3 (5%, 20 mL). The organic layer was dried and concentrated to give 7-Fluoro-5,10-dioxa-4,12-diaza-tricyclo[6.3.1.0*2,6*]dodeca-2(6),3-diene-12-carboxylic acid tert-butyl ester as an oil, 150 mg, crude yield: 100%. MS: calc'd (MH+) 285, measured (MH+) 285.

Workup

  1. washwashed with aqueous NaHCO3 (5%, 20 mL)
  2. customThe organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1057f8da5ef34c27b72918d30a778dbc
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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