Ammonia → HCID 178508933, compound

HRID 399587

Reaction equation

HRID 399587 reaction equation
C([N:4](C(=O)C)[C:5]1[NH:6][C:7](=[O:14])[C:8]2[NH:9][CH:10]=[N:11][C:12]=2[N:13]=1)(=O)C.C(O[CH2:22][O:23][CH2:24][CH2:25][O:26]C(=O)C)(=O)C.N>CS(C)=O>[CH:10]1[N:11]([CH2:22][O:23][CH2:24][CH2:25][OH:26])[C:12]2[N:13]=[C:5]([NH2:4])[N:6]=[C:7]([OH:14])[C:8]=2[N:9]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 1009992-((Acetyloxy)methoxy)ethyl acetateHCID 136360183Diacetylguanine

Product 1

HCID 178508933HCID 178508933, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Matsumoto in Chem Pharm Bull, 36(3), 1153-1157 and JP 63-107982 teaches a process for the synthesis of acyclovir(Ia) by condensation of diacetyl guanine (DAG Va) with 2-oxa-1,4-butanediol diacetate (OBDDA, VIIa) in DMSO in presence of an acid catalyst to get a mixture of N-9/N-7 isomer (66:26). The former is isolated by column chromatography and deacetylated with methanolic ammonia to give acyclovir. Overall yield of acyclovir from guanine is 42%

Workup

  1. customto get
  2. additiona mixture of N-9/N-7 isomer (66:26)
  3. customThe former is isolated by column chromatography

Sources & evidence

ORD record
ord-5825b520528642f6bbfe1b0fcb252da6
Source dataset
uspto-grants-1998_10
Patent number
US05821367

Linked notes

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