Potassium Carbonate → HCID 90037471, compound

HRID 1055383Notes

Reaction equation

HRID 1055383 reaction equation
[C:1]([O:5][C:6](=[O:27])[N:7]([C@H:9]([C:11](=[O:26])[NH:12][C@H:13]1[CH2:19][S:18][C:17]2[C:20]([NH2:24])=[CH:21][CH:22]=[CH:23][C:16]=2[NH:15][C:14]1=[O:25])[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:35][C:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][CH:37]=1>CN(C=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:1]([O:5][C:6](=[O:27])[N:7]([C@H:9]([C:11](=[O:26])[NH:12][C@H:13]1[CH2:19][S:18][C:17]2[C:20]([NH2:24])=[CH:21][CH:22]=[CH:23][C:16]=2[N:15]([CH2:35][C:36]2[C:45]3[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH:39]=[CH:38][CH:37]=2)[C:14]1=[O:25])[CH3:10])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1378441-(Bromomethyl)naphthaleneHCID 90036904HCID 90036904, compound

Product 1

HCID 90037471HCID 90037471, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (S)-1-((R)-9-amino-4-oxo-2,3,4,5-tetrahydro-benzo[b][1,4]thiazepin-3-ylcarbamoyl)-ethyl-methyl-carbamic acid tert-butyl ester (1.5 g, 3.9 mmol) in DMF (25 mL) was added K2CO3 (2.6 g, 19.0 mmol) and 1-bromomethyl-naphthalene (631 mg, 2.9 mmol) in DMF (10 mL) was added dropwise. After 36 h, the mixture was diluted with sat. aq. citric acid and extracted with EtOAc. The combined extracts were washed with H2O, brine, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography to give the title compound (1.3 g, 81%).

Workup

  1. additionwas added dropwise
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-cec326dd8e234888833116d98620aa06
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

Loading…