Triethylamine → HCID 67972701, compound

HRID 1771921Notes

Reaction equation

HRID 1771921 reaction equation
[NH2:1][CH:2]1[CH2:8][O:7][CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.CCN(CC)CC.[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](Cl)=[O:29]>>[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([NH:1][CH:2]1[CH2:8][O:7][CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1)=[O:29]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 5211735-Bromovaleryl chlorideHCID 44119210tert-Butyl 6-amino-1,4-oxazepane-4-carboxylate

Product 1

HCID 67972701HCID 67972701, compound

Procedure

To an ice bath stirring solution of tert-butyl 6-amino-1,4-oxazepane-4-carboxylate 38.4 (1.01 g, 4.67 mmol) and Et3N (1.95 mL, 14.0 mmol) was added 5-bromo-pentanoyl chloride (0.62 mL, 4.7 mmol). The ice bath was removed and the solution was stirring for 1 h and then diluted with water and extracted with DCM. The organic phase was washed with diluted citric acid, water, sat. NaHCO3, dried (MgSO4), filtered and concentrated in vacuo to afford an oil which was purification by flash column chromatography (gradient EtOAc/hexanes). LCMS m/z 324.1 & 325.1 [M−tBu]+.

Workup

  1. customThe ice bath was removed
  2. additiondiluted with water
  3. extractionextracted with DCM
  4. washThe organic phase was washed with diluted citric acid, water, sat. NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford an oil which
  9. custompurification by flash column chromatography (gradient EtOAc/hexanes)

Sources & evidence

ORD record
ord-eb1af6d47aca4a629a2a766c0679670b
Source dataset
uspto-grants-2016_02
Patent number
US09249146B2

Reaction notes

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