Dicyclohexylcarbodiimide → HCID 22828235, compound

HRID 1633306Notes

Reaction equation

HRID 1633306 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]1[O:8][C@@H:7]([N:9]2[CH:17]=[N:16][C:15]3[C:10]2=[N:11][CH:12]=[N:13][C:14]=3[NH2:18])[C@H:6]([OH:19])[C@@H:5]1[NH2:20].[C:22]([O:26][C:27]([NH:29][CH:30]([C:39](O)=[O:40])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.O>[NH2:18][C:14]1[N:13]=[CH:12][N:11]=[C:10]2[C:15]=1[N:16]=[CH:17][N:9]2[C@@H:7]1[O:8][C@H:4]([C:3]([O:2][CH3:1])=[O:21])[C@@H:5]([NH:20][C:39](=[O:40])[CH:30]([CH2:31][C:32]2[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=2)[NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:28])[C@H:6]1[OH:19]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 41648972-(((Tert-butoxy)carbonyl)amino)-3-(4-chlorophenyl)propanoic acidHCID 54526695HCID 54526695, compound

Product 1

HCID 22828235HCID 22828235, compoundYield 35.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl-1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-amino-β-D-ribofuranuronate (294 mg) prepared in Example 62, N-tert-butoxycarbonyl-β-(4-chlorophenyl)-D,L-alanine (300 mg) and N,N'-dicyclohexylcarbodiimide (206 mg) in tetrahydrofuran (15 ml) and water (5 ml) was stirred overnight. The mixture was diluted with water (50 ml) and extracted with ethyl acetate. The extract was washed with water, dried, and evaporated to dryness. The residue was subjected to column chromatography on silica gel. The elution was carried out with a mixed solvent (chloroform/methanol=97/3). The eluate was evaporated to dryness to give methyl 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-[N-tert-butoxycarbonyl-β-(4-chlorophenyl)-D,L-alanylamino]-β-D-ribofuranuronate (203 mg), mp. 120°-125° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customevaporated to dryness
  5. washThe elution
  6. customThe eluate was evaporated to dryness

Sources & evidence

ORD record
ord-16100e2a11cb4fbab579b8d51d43be9f
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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