Phthalimide → HCID 69417417, compound

HRID 1374071

Reaction equation

HRID 1374071 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:20]1(=[O:30])[NH:24][C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12.[C:31]([NH:39][C:40]1[C:41]2[N:42]=[CH:43][N:44]([C:53]=2[N:54]=[CH:55][N:56]=1)[C@@H:45]1[O:52][C@H:49]([CH2:50]O)[C@@H:47]([OH:48])[CH2:46]1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.ClCCl>[C:20]1(=[O:30])[N:24]([CH2:50][C@H:49]2[O:52][C@@H:45]([N:44]3[C:53]4[N:54]=[CH:55][N:56]=[C:40]([NH:39][C:31](=[O:38])[C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:41]=4[N:42]=[CH:43]3)[CH2:46][C@@H:47]2[OH:48])[C:23](=[O:25])[C:22]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:21]12

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 107558N-benzoyl-2'-deoxyadenosine

Product 1

HCID 69417417HCID 69417417, compoundYield 30.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 13.11 g (50 mmol) Ph3P, 6.99 g (47.5 mmol) phthalimide and 17.77 g (50 mmol) N6-benzoyl-2′-deoxyadenosine in 400 mL dry THF was added 9.84 mL (50 mmol) of diisopropyl azodicarboxylate under a nitrogen atmosphere. The resulting mixture was stirred for 2 h in an ice water bath and then 4 h at room temperature. After most of the THF was evaporated under reduced pressure, the oily residue was added 100 ml of dichloromethane. The precipitate, which was formed after the addition of dichloromethane, was filtered and washed with small amounts of THF/dichloromethane mixture (1:1). The filtrate was concentrated and purified with a silica gel column chromatography (dichloromethane/THF=2:1 then dichloromethane/methanol=19:1) to give 7.1 g of compound 2.

Workup

  1. custom4 h
  2. customat room temperature
  3. customAfter most of the THF was evaporated under reduced pressure
  4. additionthe oily residue was added 100 ml of dichloromethane
  5. customThe precipitate, which was formed
  6. filtrationwas filtered
  7. washwashed with small amounts of THF/dichloromethane mixture (1:1)
  8. concentrationThe filtrate was concentrated
  9. custompurified with a silica gel column chromatography (dichloromethane/THF=2:1

Sources & evidence

ORD record
ord-8891f53e7a104fb595b49ea395a65130
Source dataset
uspto-grants-2007_01
Patent number
US07164014B2

Linked notes

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