Acetic Anhydride → HCID 86748229, compound

HRID 1900327Notes

Reaction equation

HRID 1900327 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-73c36a422d364d22bb970b44eb64be13
Source dataset
uspto-grants-1996_11
Patent number
US05574164

Reaction notes

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