Acetic Anhydride → HCID 86748229, compound

HRID 1734830Notes

Reaction equation

HRID 1734830 reaction equation
[CH2:1]([C:13]1[S:17][C:16]([CH:18]([OH:26])[CH:19]([NH:22][C:23](=[O:25])[CH3:24])[CH2:20][OH:21])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[C:27](OC(=O)C)(=[O:29])[CH3:28].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[O:50]1CC[CH2:52][CH2:51]1>>[CH2:1]([C:13]1[S:17][C:16]([CH:18]([O:26][C:51](=[O:50])[CH3:52])[CH:19]([NH:22][C:23](=[O:25])[CH3:24])[CH2:20][O:21][C:27](=[O:29])[CH3:28])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 5

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 86748230HCID 86748230, compound

Product 1

HCID 86748229HCID 86748229, compoundYield 93.5%

Procedure

A solution of erythro N-[1-[5-(1-dodecyl)-2-thienyl]-1,3-dihydroxy-2-propyl]acetamide (12.0 g), acetic anhydride (19.2 g), triethylamine (28.4 g), and dimethylaminopyridine (0.4 g) in dry tetrahydrofuran (150 ml) was stirred at ambient temperature for 3 hrs. The reaction mixture was evaporated and the residue was dissolved in chloroform. The solution was washed with water, dried, filtered, and the filtrate was evaporated. The residue was dried to give 13.6 g (93.5%) of product, mp 105°-107° C.

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe solution was washed with water
  4. customdried
  5. filtrationfiltered
  6. customthe filtrate was evaporated
  7. customThe residue was dried

Sources & evidence

ORD record
ord-f826e807893244c48a4f433dc236aba8
Source dataset
uspto-grants-1996_07
Patent number
US05534640

Reaction notes

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