Di-tert-butyl dicarbonate → 1,1-dimethylethyl 9-[(phenylmethyl)oxy]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

HRID 1514222Notes

Reaction equation

HRID 1514222 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:19]3[O:18][CH2:17][CH2:16][NH:15][CH2:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:20](C(OC(C)(C)C)=O)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=O>C(Cl)Cl>[C:1]1([CH2:7][O:8][C:9]2[C:19]3[O:18][CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:20])[CH2:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 594035049-[(Phenylmethyl)oxy]-2,3,4,5-tetrahydro-1,4-benzoxazepine

Product 1

HCID 594034471,1-dimethylethyl 9-[(phenylmethyl)oxy]-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9-[(Phenylmethyl)oxy]-2,3,4,5-tetrahydro-1,4-benzoxazepine (Preparation 60) (7.01 g, 27.5 mmol) and BOC2O (7.01 ml, 30.2 mmol) were dissolved in DCM (100 ml) and left at room temperature for one hour then evaporated and biotage chromatographed in 5% EtOAc in hexane to remove excess BOC2O and changing to 15% EtOAc in iso-hexane to elute the title compound (8.25 g) as a white solid. MS (ES): C21H25NO4 requires 355; found 256 [M+H−100]+.

Workup

  1. customthen evaporated
  2. custombiotage chromatographed in 5% EtOAc in hexane
  3. customto remove excess BOC2O
  4. washto elute the title compound (8.25 g) as a white solid

Sources & evidence

ORD record
ord-5f2dff7c2db74f0dab078b66c526f37e
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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