Acetic Anhydride → HCID 68561794, compound

HRID 20417Notes

Reaction equation

HRID 20417 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]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=2)[CH2:19][O:18][C@@H:17]([O:34][CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37])[C@@H:16]1[CH3:40])=[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:25]=[C:26]([F:31])[CH:27]=[C:28]([F:30])[CH:29]=2)[CH2:19][O:18][C@@H:17]([O:34][CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37])[C@@H:16]1[CH3:40])=[O:14])([CH3:10])([CH3:9])[CH3:11]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68559589(2R,3S,5R)-5-[(1R,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 68561794HCID 68561794, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add acetic anhydride (0.084 ml, 0.89 mmol) to a solution of (2R,3S,5R)-5-[(1R,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-(2,2-dimethylpropoxy)-3-methylmorpholine-4-carboxylic acid tert-butyl ester (400 mg, 0.85 mmol) in dry dichloromethane (9 mL). Add triethylamine (0.179 mL, 1.27 mmol), stir 1 hour at room temperature, concentrate and purify (silica gel cartridge chromatography, eluting with 1:1 hexanes:ethyl acetate) to give the title compound as a white solid (397 mg, 91%).

Workup

  1. concentrationconcentrate
  2. custompurify
  3. wash(silica gel cartridge chromatography, eluting with 1:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-8fe81d2a5e244a32b1cf414d31deaf69
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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