Acetic Anhydride → HCID 68561129, compound

HRID 20473Notes

Reaction equation

HRID 20473 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:33])[C@@H:22]([NH2:32])[CH2:23][C:24]2[CH:29]=[C:28]([OH:30])[CH:27]=[C:26]([F:31])[CH:25]=2)[CH2:19][O:18][C@H:17]([O:34][C:35]([CH2:39][F:40])([CH3:38])[CH2:36][F:37])[CH2:16]1)=[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:33])[C@@H:22]([NH:32][C:1](=[O:3])[CH3:2])[CH2:23][C:24]2[CH:29]=[C:28]([OH:30])[CH:27]=[C:26]([F:31])[CH:25]=2)[CH2:19][O:18][C@H:17]([O:34][C:35]([CH2:36][F:37])([CH3:38])[CH2:39][F:40])[CH2:16]1)=[O:14])([CH3:10])([CH3:11])[CH3:9]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68562782HCID 68562782, compound

Product 1

HCID 68561129HCID 68561129, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add acetic anhydride (2.13 mmoles; 201.52 μL) to a solution of (2R,5R)-5-[(1S,2S)-2-amino-3-(3-fluoro-5-hydroxy-phenyl)-1-hydroxy-propyl]-2-(2-fluoro-1-fluoromethyl-1-methyl-ethoxy)-morpholine-4-carboxylic acid tert-butyl ester (2.03 mmoles; 1.00 g) and triethylamine (2.23 mmoles; 311.29 μL) in 10 mL dichloromethane at 0° C. (ice bath) and stir the mixture at 0° C. for 1 h. Concentrate under reduced pressure and subject residue to silica gel chromatography eluting with 40:60 to 0:100 hexane/ethyl acetate gradient to give the desired compound as white solid (950.00 mg, 87.53%).

Workup

  1. concentrationConcentrate under reduced pressure
  2. washeluting with 40:60 to 0:100 hexane/ethyl acetate gradient

Sources & evidence

ORD record
ord-b3a1e75c7a4d4006afddaa4c4daa6522
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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