Trifluoroacetic acid → HCID 476134, compound

HRID 1633307Notes

Reaction equation

HRID 1633307 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:16][C@H:15]([C:17]([O:19]C)=[O:18])[C@@H:14]([NH:21][C:22](=[O:40])[CH:23]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[NH:24]C(OC(C)(C)C)=O)[C@H:12]1[OH:13].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(OCC)C>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:16][C@H:15]([C:17]([OH:19])=[O:18])[C@@H:14]([NH:21][C:22](=[O:40])[CH:23]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[NH2:24])[C@H:12]1[OH:13]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 22828235HCID 22828235, compound

Product 1

HCID 476134HCID 476134, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of methyl 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-[N-tert-butoxycarbonyl-β-(4-chlorophenyl)-D,L-alanylamino]-β-D-ribofuranuronate (150 mg) prepared in Example 64 and anisol (0.3 ml) was stirred in an ice-bath, and trifluoroacetic acid (3 ml) was added. After stirring for 1 hour in an ice-bath, diethyl ether was added to the mixture. The resulting precipitates were collected by filtration, added to 1N sodium hydroxide (3 ml), and stirred for 30 minutes in an ice-bath. The reaction mixture was neutralized with 1N hydrochloric acid, subjected to column chromatography on a non-ionic adsorption resin "HP-20" (trade mark, Mitsubishi Chemical Industries Ltd.) (30 ml). After the column was washed with water, the elution was carried out with 50% aqueous methanol. The eluate was evaporated to remove methanol under reduced pressure and lyophilized to give 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-[β-(4-chlorophenyl)-D,L-alanylamino]-β-D-ribofuranuronic acid (82 mg), mp. 170°-178° C. (dec.).

Workup

  1. stirringAfter stirring for 1 hour in an ice-bath
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. additionadded to 1N sodium hydroxide (3 ml)
  5. stirringstirred for 30 minutes in an ice-bath
  6. washAfter the column was washed with water
  7. washthe elution
  8. customThe eluate was evaporated
  9. customto remove methanol under reduced pressure

Sources & evidence

ORD record
ord-716c1e05a0c541d5b94ca65d72e875a7
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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