Butylamine → N-[5-(6-Aminopurin-9-yl)-2-(N-butylcarbamoyl)-4-hydroxyoxolan-3-yl]-2-[(butylamino)carbonylamino]-3-(4-methoxyphenyl)propanamide

HRID 1633305Notes

Reaction equation

HRID 1633305 reaction equation
C([NH:9][C:10]1[N:18]=[CH:17][N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[C@@H:19]1[O:24][C@H:23]([C:25](OC)=[O:26])[C@@H:22]([NH:29][C:30](=[O:52])[C@H:31]([CH2:43][C:44]2[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=2)[NH:32][C:33]([O:35]CC2C=CC=CC=2)=O)[C@H:20]1[OH:21])(=O)C1C=CC=CC=1.[CH2:53]([NH2:57])[CH2:54][CH2:55][CH3:56]>CO>[CH2:53]([NH:57][C:25](=[O:26])[C@H:23]1[O:24][C@@H:19]([N:14]2[CH:13]=[N:12][C:11]3[C:15]2=[N:16][CH:17]=[N:18][C:10]=3[NH2:9])[C@H:20]([OH:21])[C@@H:22]1[NH:29][C:30](=[O:52])[C@H:31]([CH2:43][C:44]1[CH:49]=[CH:48][C:47]([O:50][CH3:51])=[CH:46][CH:45]=1)[NH:32][C:33](=[O:35])[NH:14][CH2:19][CH2:20][CH2:22][CH3:23])[CH2:54][CH2:55][CH3:56]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 22828238methyl 1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-beta-D-ribofuranuronate

Product 1

HCID 476143N-[5-(6-Aminopurin-9-yl)-2-(N-butylcarbamoyl)-4-hydroxyoxolan-3-yl]-2-[(butylamino)carbonylamino]-3-(4-methoxyphenyl)propanamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 1-(6-benzoylamino-9H-purin -9-yl)-1,3-dideoxy-3-(N-benzyloxycarbonyl-O-methyl-L-tyrosylamino)-β-D-ribofuranuronate prepared in Example 56 (355 mg), n-butylamine (5 ml) and methanol (5 ml) was refluxed for 9 hours. The mixture was evaporated to dryness and the residue was triturated in diethyl ether to give N-n-butyl-1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-(N-n-butylcarbamoyl-O-methyl-L-tyrosylamino)-β-D-ribofuranuronamide (208 mg), mp. 111°-115° C. (dec.).

Workup

  1. temperaturewas refluxed for 9 hours
  2. customThe mixture was evaporated to dryness
  3. customthe residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-f2e3eab3fcf649318ccfd418141ea481
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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