Acetic Anhydride → HCID 511577, compound

HRID 989604Notes

Reaction equation

HRID 989604 reaction equation
CC[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][C:17]([C:20]([N:22]1[CH:26]([C:27]([NH:29][C@H:30]([C:35]([NH:37][C@H:38]([C:42]([NH:44][C@H:45]([C:51]([NH:53][C@H:54]([CH2:59][OH:60])[CH2:55][CH:56]([CH3:58])[CH3:57])=[O:52])[CH2:46][CH2:47][C:48]([NH2:50])=[O:49])=[O:43])[CH:39]([CH3:41])[CH3:40])=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33])=[O:28])[CH2:25][C@H:24]([OH:61])[CH2:23]1)=[O:21])([CH3:19])[CH3:18])=[O:15].C(OC(=O)C)(=O)C>N1C=CC=CC=1>[CH3:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][C:17]([C:20]([N:22]1[CH:26]([C:27]([NH:29][C@H:30]([C:35]([NH:37][C@H:38]([C:42]([NH:44][C@H:45]([C:51]([NH:53][C@H:54]([CH2:59][OH:60])[CH2:55][CH:56]([CH3:58])[CH3:57])=[O:52])[CH2:46][CH2:47][C:48]([NH2:50])=[O:49])=[O:43])[CH:39]([CH3:41])[CH3:40])=[O:36])[CH2:31][CH:32]([CH3:33])[CH3:34])=[O:28])[CH2:25][C@H:24]([OH:61])[CH2:23]1)=[O:21])([CH3:19])[CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 511574HCID 511574, compound

Product 1

HCID 511577HCID 511577, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 13.3 mg of Halovir A in 0.5 mL of pyridine was added 0.5 mL of acetic anhydride and 1.2 mg of N,N-dimethylaminopyridine. The reaction mixture was stirred under nitrogen at ambient temperature for 16 hours. The solvent was removed in vacuo, and the crude mixture was partitioned between 3 mL of saturated sodium bicarbonate and 3 mL of ethyl acetate. The layers were separated and the aqueous layer was washed with 2×3 mL of ethyl acetate. The organic layers were combined and washed with 5 mL each of 1 N HCl and brine, dried over Na2CO3, filtered, and concentrated in vacuo. The crude product was purified by C18 HPLC using 2.5% H2O in methanol. Pure Halovir D was obtained as a colorless oil and was characterized by mass spectrometry, and proton and carbon NMR spectroscopy.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude mixture was partitioned between 3 mL of saturated sodium bicarbonate and 3 mL of ethyl acetate
  3. customThe layers were separated
  4. washthe aqueous layer was washed with 2×3 mL of ethyl acetate
  5. washwashed with 5 mL each of 1 N HCl and brine
  6. dry with materialdried over Na2CO3
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by C18 HPLC

Sources & evidence

ORD record
ord-4af969e8090f4ae9816d1668d34f3974
Source dataset
uspto-grants-2002_10
Patent number
US06458766B1

Reaction notes

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