Benzyl chloroformate → HCID 89649152, compound

HRID 1774001Notes

Reaction equation

HRID 1774001 reaction equation
[F:1][C:2]1[C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=2[C:5]([OH:13])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>CN(C=O)C.C(Cl)Cl>[CH2:27]([O:26][C:24]([N:10]1[CH2:9][CH2:8][C:7]2[C:2]([F:1])=[CH:3][CH:4]=[C:5]([OH:13])[C:6]=2[CH2:12][CH2:11]1)=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 89648453HCID 89648453, compound

Product 1

HCID 89649152HCID 89649152, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To an ice-cooled solution of 9-fluoro-2,3,4,5-tetrahydro-1H-benzo[d]azepin-6-ol (550 mg, 3.04 mmol, 1.0 eq.) and DIPEA (1.56 mL, 9.11 mmol, 3.0 eq.) in a mixture of DMF/DCM 1:2 (30 mL), benzyl chloroformate (0.50 mL, 3.34 mmol, 1.1 eq.) was added dropwise. Upon completion of the addition, the cooling bath was removed and the solution was stirred at r.t. for 3 hours. Then 1M aq. NaOH soln. (10 mL) was added ant the reaction mixture was stirred at r.t. for 1 hour. The mixture was extracted with DCM (3×50 mL). The comb. org. phases were dried over MgSO4 and concentrated in vacuo. The residue was purified by prep. HPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions) and concentrated in vacuo to give the title compound as a brown solid.

Workup

  1. additionwas added dropwise
  2. additionUpon completion of the addition
  3. customthe cooling bath was removed
  4. addition(10 mL) was added ant the reaction mixture
  5. stirringwas stirred at r.t. for 1 hour
  6. extractionThe mixture was extracted with DCM (3×50 mL)
  7. dry with materialphases were dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by prep
  10. concentrationHPLC (column: Atlantis, 30×75 mm, 10 um, UV/MS, acidic conditions) and concentrated in vacuo

Sources & evidence

ORD record
ord-f9637c5caec441c3b857d68e435eb45a
Source dataset
uspto-grants-2016_02
Patent number
US09255090B2

Reaction notes

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