Water → HCID 118574037, compound

HRID 1055367Notes

Reaction equation

HRID 1055367 reaction equation
O[Li].O.O.[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([CH2:16][N:17]1[C:23](=[O:24])[C@@H:22]([NH:25][C:26](=[O:38])[C@@H:27]([N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH3:30])[CH3:28])[CH2:21][O:20][C:19]3[C:39]([C:43]([O:45]C)=[O:44])=[CH:40][CH:41]=[CH:42][C:18]1=3)=[C:11]([O:47][CH3:48])[CH:10]=[CH:9]2>CO>[Br:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([CH2:16][N:17]1[C:23](=[O:24])[C@@H:22]([NH:25][C:26](=[O:38])[C@@H:27]([N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:35])[CH3:36])=[O:32])[CH3:30])[CH3:28])[CH2:21][O:20][C:19]3[C:39]([C:43]([OH:45])=[O:44])=[CH:40][CH:41]=[CH:42][C:18]1=3)=[C:11]([O:47][CH3:48])[CH:10]=[CH:9]2

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 118574239HCID 118574239, compound

Product 1

HCID 118574037HCID 118574037, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

LiOH.H2O (31.3 mg, 746 μmol, Eq: 2.5) and H2O (1.00 mL) was added to a solution of (S)-methyl 5-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-3-((S)-2-(tert-butoxycarbonyl (methyl)amino)propanamido)-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine-9-carboxylate (200 mg, 298 μmol, Eq: 1.00) in MeOH (6.0 mL) and the mixture heated to 50° C. After 90 min. the mixture was concentrated, diluted with H2O and extracted with Et2O. The combined Et2O extracts were extracted with 5% NaHCO3. The combined aqueous mixture was acidified to pH 2.0 with 1 N HCl, extracted with EtOAc and the combined organic extracts washed with brine, dried over Na2SO4 and concentrated to afford the title compound (180 mg, 91%) as an off white foam which was used without purification.

Workup

  1. concentrationAfter 90 min. the mixture was concentrated
  2. additiondiluted with H2O
  3. extractionextracted with Et2O
  4. extractionThe combined Et2O extracts were extracted with 5% NaHCO3
  5. extractionextracted with EtOAc
  6. washthe combined organic extracts washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ba1c302e471f4816ad7deb6a4aab0306
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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