Acetic Anhydride → HCID 23277624, compound

HRID 372622Notes

Reaction equation

HRID 372622 reaction equation
[NH2:1][C:2]1[C:10]([CH2:11][CH2:12][CH:13]([CH3:41])[CH:14]([OH:40])[CH:15]([CH3:39])[C:16](=[O:38])[CH:17]([CH2:36][CH3:37])[CH:18]2[CH:22]([CH3:23])[CH2:21][C:20]([CH2:34][CH3:35])([CH:24]3[CH2:29][CH2:28][C:27]([CH2:31][CH3:32])([OH:30])[CH:26]([CH3:33])[O:25]3)[O:19]2)=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:42])=[C:4]([CH3:43])[CH:3]=1.[C:44](OC(=O)C)(=[O:46])[CH3:45].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[C:44]([NH:1][C:2]1[C:10]([CH2:11][CH2:12][CH:13]([CH3:41])[CH:14]([OH:40])[CH:15]([CH3:39])[C:16](=[O:38])[CH:17]([CH2:36][CH3:37])[CH:18]2[CH:22]([CH3:23])[CH2:21][C:20]([CH2:34][CH3:35])([CH:24]3[CH2:29][CH2:28][C:27]([CH2:31][CH3:32])([OH:30])[CH:26]([CH3:33])[O:25]3)[O:19]2)=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:42])=[C:4]([CH3:43])[CH:3]=1)(=[O:46])[CH3:45]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 23277598HCID 23277598, compound

Product 1

HCID 23277624HCID 23277624, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 1.21 g. (2 mmole) of 5-amino-3-methyl-6-{7-ethyl-4-hydroxy-3,5-dimethyl-6-oxo-7-[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]-heptyl}salicylic acid in 50 ml. glacial acetic acid was added 1 ml. acetic anhydride (~10 mmoles). On warming the mixture to 70° on a steam bath, the amine dissolved and after a further half an hour at room temperature, the solution was poured on to crushed ice. The mixture was carefully made alkaline with sodium carbonate solution and extracted twice with 400 ml. ether. After drying (NaSO4) the ethereal solution was evaporated to approximately 100 ml. The resulting microcrystalline product had m.p. 189-190°, [α]D -17.45° (1 percent, MeOH).

Workup

  1. additionTo a suspension of 1.21 g
  2. temperatureOn warming the mixture to 70° on a steam bath
  3. additionthe solution was poured on
  4. customto crushed ice
  5. extractionextracted twice with 400 ml
  6. dry with materialAfter drying (NaSO4) the ethereal solution
  7. customwas evaporated to approximately 100 ml

Sources & evidence

ORD record
ord-1bb0f8a8e23f4d3f87d9fa969968ec55
Source dataset
uspto-grants-1978_05
Patent number
USRE029651

Reaction notes

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