Acetic Anhydride → HCID 68563963, compound

HRID 20483Notes

Reaction equation

HRID 20483 reaction equation
C(N(CC)CC)C.[C:8](OC(=O)C)(=[O:10])[CH3:9].[C:15]([O:19][C:20]([N:22]1[CH:27]([CH:28]([OH:43])[CH:29]([NH2:42])[CH2:30][C:31]2[CH:36]=[C:35]([O:37][CH2:38][CH2:39][CH3:40])[CH:34]=[C:33]([F:41])[CH:32]=2)[CH2:26][O:25][CH:24]([O:44][CH2:45][C:46]([CH2:50][F:51])([CH3:49])[CH2:47][F:48])[CH:23]1[CH3:52])=[O:21])([CH3:18])([CH3:17])[CH3:16]>ClCCl>[C:15]([O:19][C:20]([N:22]1[CH:27]([CH:28]([OH:43])[CH:29]([NH:42][C:8](=[O:10])[CH3:9])[CH2:30][C:31]2[CH:36]=[C:35]([O:37][CH2:38][CH2:39][CH3:40])[CH:34]=[C:33]([F:41])[CH:32]=2)[CH2:26][O:25][CH:24]([O:44][CH2:45][C:46]([CH2:50][F:51])([CH3:49])[CH2:47][F:48])[CH:23]1[CH3:52])=[O:21])([CH3:16])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 68561375HCID 68561375, compound

Product 1

HCID 68563963HCID 68563963, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add triethyl amine (0.025 mL) and acetic anhydride (0.013 mL) to a solution of 5-[2-amino-3-(3-fluoro-5-propoxy-phenyl)-1-hydroxy-propyl]-2-(3-fluoro-2-fluoromethyl-2-methyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester (67 mg) in dichloromethane (2 mL). Stir at room temperature for 2 hours. Concentrate under reduced pressure and subject to silica gel chromatography, eluting with a linear gradient from hexanes to ethyl acetate to afford 5-[2-acetylamino-3-(3-fluoro-5-propoxy-phenyl)-1-hydroxy-propyl]-2-(3-fluoro-2-fluoromethyl-2-methyl-propoxy)-3-methyl-morpholine-4-carboxylic acid tert-butyl ester (49 mg, 68%)

Workup

  1. concentrationConcentrate under reduced pressure
  2. washeluting with a linear gradient from hexanes to ethyl acetate

Sources & evidence

ORD record
ord-db1f01b015794eb49d42baf7a9a35760
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Reaction notes

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