Acetic Anhydride → HCID 68561563, compound

HRID 20474Notes

Reaction equation

HRID 20474 reaction equation
C(N(CC)CC)C.[C:8](OC(=O)C)(=[O:10])[CH3:9].[C:15]([O:19][C:20]([N:22]1[CH:27]([C@@H:28]([OH:40])[C@@H:29]([NH2:39])[CH2:30][C:31]2[CH:36]=[C:35]([F:37])[CH:34]=[C:33]([F:38])[CH:32]=2)[CH2:26][O:25][CH:24]([O:41][CH2:42][CH3:43])[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>O1CCCC1.C(OCC)(=O)C>[C:15]([O:19][C:20]([N:22]1[C@@H:27]([C@@H:28]([OH:40])[C@@H:29]([NH:39][C:8](=[O:10])[CH3:9])[CH2:30][C:31]2[CH:32]=[C:33]([F:38])[CH:34]=[C:35]([F:37])[CH:36]=2)[CH2:26][O:25][C@H:24]([O:41][CH2:42][CH3:43])[CH2:23]1)=[O:21])([CH3:17])([CH3:18])[CH3:16]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 685636645-[(1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-ethoxymorpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 68561563HCID 68561563, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add triethylamine (0.030 g, 0.30 mmol) and acetic anhydride (0.024 g, 0.23 mmol) to R)-5-[(1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-ethoxymorpholine-4-carboxylic acid tert-butyl ester (0.095 g, 0.228 mmol) in tetrahydrofuran (4 mL) at room temperature. Stir 4 hours and dilute with ethyl acetate. Wash with water and saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 20:80 to 100:0 ethyl acetate:hexanes) to give the desired compound (69 mg, 66%).

Workup

  1. washWash with water and saturated aqueous sodium chloride
  2. dry with materialdry (magnesium sulfate)
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with 20:80 to 100:0 ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-2ec5f9c03e4f4a1cacc0c425d3201b33
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

Loading…