Water → HCID 118236081, compound

HRID 1481301Notes

Reaction equation

HRID 1481301 reaction equation
[OH:1][CH:2]1[C:3](=[O:34])[NH:4][C:5]2[CH:6]=[C:7]([NH:29][C:30]([O:32][CH3:33])=[O:31])[CH:8]=[CH:9][C:10]=2[C:11]2[CH:28]=[C:15]([C@@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:17][CH:18]=[CH:19]1)[N:14]=[CH:13][CH:12]=2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.O>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:33][O:32][C:30]([NH:29][C:7]1[CH:6]=[C:5]2[C:10]([C:11]3[CH:12]=[CH:13][N:14]=[C:15]([CH:28]=3)[C@@H:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:26])[CH3:25])[CH2:17][CH2:18][CH2:19][C:2](=[O:1])[C:3](=[O:34])[NH:4]2)=[CH:9][CH:8]=1)=[O:31]

Participants

6

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 118236077HCID 118236077, compound

Product 1

HCID 118236081HCID 118236081, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 123B (360 mg, 0.765 mmol) in DCM (7.5 mL) was added Dess-MartinPeriodinane (357 mg, 0.842 mmol) and stirred at rt. After 1 hr, the reaction mixture was diluted with a small amount of sat. NaHCO3 and some water was added. The reaction mixture was extracted with DCM (3×). The combined organic extracts were washed with brine, dried (Na2SO4), filtered, and concentrated. This material was used in the next step without purification. MS (ESI) m/z: 487.2 (M+H2O+H)+.

Workup

  1. extractionThe reaction mixture was extracted with DCM (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThis material was used in the next step without purification

Sources & evidence

ORD record
ord-5b16531f2df34e57b3260638c27aadd0
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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