Acetic Anhydride → HCID 68561123, compound

HRID 20458Notes

Reaction equation

HRID 20458 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[C:8]([O:12][C:13]([N:15]1[C@@H:20]([C@@H:21]([OH:36])[C@@H:22]([NH2:35])[CH2:23][C:24]2[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([O:31][CH2:32][CH2:33][CH3:34])[CH:25]=2)[CH2:19][O:18][C@@H:17]([O:37][CH2:38][C:39]([CH3:43])([CH3:42])[CH2:40][F:41])[C@@H:16]1[CH3:44])=[O:14])([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C>ClCCl>[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]([F:30])[CH:27]=[C:26]([O:31][CH2:32][CH2:33][CH3:34])[CH:25]=2)[CH2:19][O:18][C@@H:17]([O:37][CH2:38][C:39]([CH3:42])([CH3:43])[CH2:40][F:41])[C@@H:16]1[CH3:44])=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68562634HCID 68562634, compound

Product 1

HCID 68561123HCID 68561123, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add acetic anhydride (43 μL, 0.44 mmol) to a solution of (2R,3S,5R)-5-[(1S,2S)-1-Hydroxy-2-amino-3-(3-propoxy-5-fluorophenyl)-propyl]-2-(3-fluoro-2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester (231 mg, 0.44 mmol) and triethylamine (92 μL, 0.65 mmol) in dichloromethane (4.6 mL) and stir at room temperature for 30 minutes. Concentrate reaction mixture under a stream of nitrogen and subject residue to silica gel chromatography, eluting with 0-100% ethyl acetate in hexane to provide the title compound.

Workup

  1. concentrationConcentrate
  2. customreaction mixture under a stream of nitrogen
  3. washeluting with 0-100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-2656e144b7c2482d98ec54da4e770fbd
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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