Acetic Acid Mixture with Hydrobromic Acid → HCID 90037310, compound

HRID 1055391Notes

Reaction equation

HRID 1055391 reaction equation
[CH3:1][C:2]1([CH3:25])[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][C:4](=[O:13])[CH:3]1[NH:14]C(=O)OCC1C=CC=CC=1.Br.CC(O)=O>CCOCC>[NH2:14][CH:3]1[C:2]([CH3:1])([CH3:25])[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][C:4]1=[O:13]

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 90037631HCID 90037631, compound

Product 1

HCID 90037310HCID 90037310, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Benzyl 2,2-dimethyl-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-3-ylcarbamate (0.67 g, 1.88 mmol, Eq: 1.00, WO96/11940) and 33% HBr/HOAc (9 μl, 54.7 mmol, Eq: 29) were combined to give a yellow solution. After 75 min. the mixture was diluted with 100 mL Et2O. The resulting precipitate was collected by filtration, washed with Et2O and added to 100 mL of aq. NaHCO3. The mixture was extracted with EtOAc and DCM. The combined extracts were dried over Na2SO4, filtered and the filtrate concentrated to give the title compound as a white solid (0.3370 g, 81%) which was used without purification. MS m/z 379.0 (MH+).

Workup

  1. customto give a yellow solution
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with Et2O
  4. additionadded to 100 mL of aq. NaHCO3
  5. extractionThe mixture was extracted with EtOAc and DCM
  6. dry with materialThe combined extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-ef6b9d58064b4a938f3f57c1a290e137
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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