Methanol → HCID 53769624, compound

HRID 704647Notes

Reaction equation

HRID 704647 reaction equation
[OH:1][CH:2]([CH:5]1[CH2:7][CH:6]1[N:8]1[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]1=[O:10])[CH2:3][OH:4].C(N([CH2:22][CH3:23])CC)C.[C:24](OC(=O)C)(=[O:26])[CH3:25].C[OH:32]>C(#N)C.CN(C)C1C=CN=CC=1>[C:24]([O:1][CH:2]([CH:5]1[CH2:7][CH:6]1[N:8]1[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]1=[O:10])[CH2:3][O:4][C:22](=[O:32])[CH3:23])(=[O:26])[CH3:25]

Participants

7

Reactant 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 54002130HCID 54002130, compound

Product 1

HCID 53769624HCID 53769624, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 176 mg (0.78 mmol) of the product of Example 16 in 10 mL of acetonitrile is added 0.287 mL (2.06 mmol) of triethylamine (TEA), 7 mg (0.0585 mmol) of 4-dimethylaminopyridine (DMAP) 0.177 mL (1.87 mmol) of acetic anhydride. After 3 h at ambient temperature, the clear solution is treated with 1 mL of methanol and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel to afford the title compound.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1fa1c35b2e0047fbb80cdadd177a6a30
Source dataset
uspto-grants-1991_01
Patent number
US04988703

Reaction notes

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