Acetic Anhydride → HCID 68562312, compound

HRID 20424Notes

Reaction equation

HRID 20424 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]([F:39])([CH3:38])[CH3:37])[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]([F:30])[CH:27]=[C:26]([F:31])[CH:25]=2)[CH2:19][O:18][C@@H:17]([O:34][CH2:35][C:36]([F:39])([CH3:38])[CH3:37])[CH2:16]1)=[O:14])([CH3:9])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68559684(2S,5R)-5-[(1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-(2-fluoro-2-methylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester

Product 1

HCID 68562312HCID 68562312, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add acetic anhydride (0.084 mL, 0.91 mmol) to a solution of (2S,5R)-5-[(1S,2S)-2-amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-(2-fluoro-2-methylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester (400 mg, 0.86 mmol) and triethylamine (0.81 mL, 130 mmol) in dry dichloromethane (10 mL) at room temperature and stir for 4 hours, concentrate and purify (silica gel cartridge chromatography, eluting with 2:1 to 1:2 hexanes:ethyl acetate), to give the desired compound as a white solid (0.37 g, 80%).

Workup

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

Sources & evidence

ORD record
ord-472ea71c6c0f45a5a93e7363ce426333
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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