Lithium hydroxide, monohydrate → HCID 90060669, compound

HRID 1055368Notes

Reaction equation

HRID 1055368 reaction equation
O[Li].O.[Br:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:15][N:16]2[C:22](=[O:23])[C@@H:21]([NH:24][C:25](=[O:37])[C@@H:26]([N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH3:29])[CH3:27])[CH2:20][O:19][C:18]3[C:38]([C:42]([O:44]C)=[O:43])=[CH:39][CH:40]=[CH:41][C:17]2=3)=[CH:7][CH:6]=1>CO>[Br:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH2:15][N:16]2[C:22](=[O:23])[C@@H:21]([NH:24][C:25](=[O:37])[C@@H:26]([N:28]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH3:29])[CH3:27])[CH2:20][O:19][C:18]3[C:38]([C:42]([OH:44])=[O:43])=[CH:39][CH:40]=[CH:41][C:17]2=3)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118573983HCID 118573983, compound

Product 1

HCID 90060669HCID 90060669, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 0.1 M solution of LiOH.H2O (8.87 mL, 887 μmol, Eq: 1.00) was added to a solution of (S)-methyl 5-((4-bromonaphthalen-1-yl)methyl)-3-((S)-2-(tert-butoxycarbonyl(methyl)amino)propanamido)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-9-carboxylate (568 mg, 887 μmol, Eq: 1.00) in MeOH (10 mL) at 0° C. The mixture was stirred at RT for 20 min. then heated to 40° C. After 6.5 h the MeOH was removed in vacuo and the aqueous mixture diluted with sat. NaHCO3 and extracted with Et2O. The aqueous mixture was cooled 0° C., acidified to pH 3 with 3 N HCl and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated to afford the title compound (433 mg, 78%) as a white foam which was used without purification.

Workup

  1. temperaturethen heated to 40° C
  2. customAfter 6.5 h the MeOH was removed in vacuo
  3. additionthe aqueous mixture diluted with sat. NaHCO3
  4. extractionextracted with Et2O
  5. temperatureThe aqueous mixture was cooled 0° C.
  6. extractionextracted with EtOAc
  7. washThe combined extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e6d72d406f0f46d3a63bade5fb15bd7e
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

Loading…