Dicyclohexylcarbodiimide → HCID 136335119, compound

HRID 1170669Notes

Reaction equation

HRID 1170669 reaction equation
[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:9](=[O:20])[CH2:10][CH2:11][C:12]([O:14][CH:15]([CH2:18][OH:19])[CH2:16][OH:17])=[O:13])[O:5][C@@H:4]([N:21]2[C:31]3[N:30]=[C:28]([NH2:29])[NH:27][C:25](=[O:26])[C:24]=3[N:23]=[CH:22]2)[CH2:3]1.[C:32]([NH:42][C@H:43]([C:47](O)=[O:48])[CH:44]([CH3:46])[CH3:45])([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.CN(C=O)C>[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:9](=[O:20])[CH2:10][CH2:11][C:12]([O:14][CH:15]([CH2:16][OH:17])[CH2:18][O:19][C:47](=[O:48])[C@H:43]([CH:44]([CH3:45])[CH3:46])[NH:42][C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])=[O:13])[O:5][C@@H:4]([N:21]2[C:31]3[N:30]=[C:28]([NH2:29])[NH:27][C:25](=[O:26])[C:24]=3[N:23]=[CH:22]2)[CH2:3]1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 726987N-Carbobenzoxy-L-valineHCID 136015496HCID 136015496, compound

Product 1

HCID 136335119HCID 136335119, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2′,3′-dideoxy-3′-fluoro-5′-O-[3-(1,3-dihydroxy-2-propyloxy carbonyl)-propanoyl]guanosine (1.3 g, 2.93 mmole), N-CBZ-L-valine (1.00 g, 4 mmole), HOBT (0.54 g, 4 mmole) and DMAP (48.8 mg, 0.4 mmole) was coevaporated two times with DMF and reduced to about 60 ml. DCC (0.91 g, 4.4 mmole) was added and the mixture was stirred for 72 hours at room temperature. The mixture was filtered and the solution evaporated under reduced pressure. Ethyl acetate (150 ml) was added and the organic phase washed twice with 5% acetic acid, 5% sodium hydrogen carbonate and water. The organic phase was dried with sodium sulfate and evaporated under reduced pressure. The product was isolated by silica gel column chromatography. Yield: 0.99 g

Workup

  1. filtrationThe mixture was filtered
  2. customthe solution evaporated under reduced pressure
  3. additionEthyl acetate (150 ml) was added
  4. washthe organic phase washed twice with 5% acetic acid, 5% sodium hydrogen carbonate and water
  5. dry with materialThe organic phase was dried with sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe product was isolated by silica gel column chromatography

Sources & evidence

ORD record
ord-94ad9f25220b4068bdb5ef1327f5050f
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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