Acetic Anhydride → HCID 68562306, compound

HRID 20439Notes

Reaction equation

HRID 20439 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([O:12][C:13]([N:15]1[C@@H:20]([CH:21]([OH:36])[CH:22]([NH2:35])[CH2:23][C:24]2[CH:29]=[C:28]([O:30][CH2:31][CH2:32][CH3:33])[CH:27]=[C:26]([F:34])[CH:25]=2)[CH2:19][O:18][C@@H:17]([O:37][CH2:38][C:39]([CH3:42])([CH3:41])[CH3:40])[C@@H:16]1[CH3:43])=[O:14])([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[C:8]([O:12][C:13]([N:15]1[C@@H:20]([C@@H:21]([OH:36])[C@@H:22]([NH:35][C:1](=[O:3])[CH3:2])[CH2:23][C:24]2[CH:29]=[C:28]([O:30][CH2:31][CH2:32][CH3:33])[CH:27]=[C:26]([F:34])[CH:25]=2)[CH2:19][O:18][C@@H:17]([O:37][CH2:38][C:39]([CH3:41])([CH3:40])[CH3:42])[C@@H:16]1[CH3:43])=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68562052HCID 68562052, compound

Product 1

HCID 68562306HCID 68562306, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add acetic anhydride (0.07 g, 0.70 mmol) to (2R,3S,5R)-5-[2-Amino-3-(3-fluoro-5-propoxy-phenyl)-1-hydroxy-propyl]-2-(2,2-dimethyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester (0.34 g, 0.66 mmol) and triethylamine (0.10 g, 0.99 mmol) in tetrahydrofuran (6 mL) at room temperature and stir 1 hour. Dilute with ethyl acetate and wash with saturated aqueous ammonium chloride and saturated aqueous sodium chloride. Dry over magnesium sulfate, filter and concentrate. Purify on 12 g silica gel eluting with 100:0 to 20:80 hexanes:ethyl acetate to give 0.175 g of the desired compound as an oil.

Workup

  1. washwash with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  2. dry with materialDry over magnesium sulfate
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify on 12 g silica gel eluting with 100:0 to 20:80 hexanes

Sources & evidence

ORD record
ord-5c556a71217b4a12af212e7e9483610d
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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