Dicyclohexylcarbodiimide → HCID 22828235, 화합물

HRID 1633306노트

반응식

HRID 1633306 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 22828235HCID 22828235, 화합물수율 35.3%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-16100e2a11cb4fbab579b8d51d43be9f
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04479942

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