Acetic Acid → HCID 73057217, compound

HRID 1055432Notes

Reaction equation

HRID 1055432 reaction equation
C([BH3-])#N.[Na+].[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:28](=[O:29])[C@@H:27]([NH:30][C:31](=[O:35])[C@@H:32]([NH2:34])[CH3:33])[C:21]3([CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[O:20][C:19]3[CH:36]=[CH:37][CH:38]=[CH:39][C:18]1=3)=[C:11]([O:40][CH3:41])[CH:10]=[CH:9]2.[CH2:42]1OC(O)C[O:44][CH:43]1O.C(O)(=O)C>CO.Cl.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:28](=[O:29])[C@@H:27]([NH:30][C:31](=[O:35])[C@@H:32]([NH:34][CH2:42][CH2:43][OH:44])[CH3:33])[C:21]3([CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[O:20][C:19]3[CH:36]=[CH:37][CH:38]=[CH:39][C:18]1=3)=[C:11]([O:40][CH3:41])[CH:10]=[CH:9]2

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 186078Glycolaldehyde dimerHCID 5003444Sodium cyanoborohydrideHCID 73057527HCID 73057527, compound

Product 1

HCID 73057217HCID 73057217, compoundYield 163.3%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium cyanoborohydride (5.14 mg, 81.8 μmol, Eq: 1.50) was added to a solution of (S)-N-((S)-5-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-4-oxo-2′,3′,4,5,5′,6′-hexahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-3-yl)-2-amino-propanamide (31 mg, 54.5 μmol, Eq: 1.00), glycolaldehyde dimer (3.6 mg, 30.0 μmol, Eq: 0.55) and acetic acid (3.27 mg, 3.15 μl, 54.5 μmol, Eq: 1.00) in MeOH (1 mL) and the mixture was stirred at RT overnight. The mixture was diluted with 1 N HCl and H2O/1 N NaOH was added to adjust the pH to ˜8-9. The mixture was extracted with EtOAc, the combined extracts were washed with brine, dried over Na2SO4 and concentrated. The resulting material was purified by flash chromatography to afford the title compound (30 mg, 90% yield). MS m/z 613.8 (MH+).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting material was purified by flash chromatography

Sources & evidence

ORD record
ord-e4e5808087584636b125b4589e80db34
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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