Ethyl Acetate → HCID 178430608, compound

HRID 2287278Notes

Reaction equation

HRID 2287278 reaction equation
[Si:1]([C@@:8]1([OH:24])[C@@H:12]([CH2:13][OH:14])[O:11][C@@H:10]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH2:9]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH:25]([N:28](C(C)C)CC)(C)C.C(CC[O:38][P:39](Cl)[N:40]([CH:44]([CH3:46])[CH3:45])[CH:41]([CH3:43])[CH3:42])#N.C(O[CH2:52][CH3:53])(=O)C>C(Cl)Cl>[C:25]([CH2:52][CH2:53][PH:39]([O:14][CH2:13][C@H:12]1[O:11][C@@H:10]([N:15]2[CH:23]=[C:21]([CH3:22])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH2:9][C@:8]1([Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3])[OH:24])([N:40]([CH:41]([CH3:42])[CH3:43])[CH:44]([CH3:45])[CH3:46])[OH:38])#[N:28]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 27348442-Cyanoethyl N,N-diisopropylchlorophosphoramiditeHCID 18664399HCID 18664399, compound

Product 1

HCID 178430608HCID 178430608, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3'-(t-butyldimethylsilyl)thymidine (1.10 g, 3.09 mmol) and diisopropylehtylamine (1.40 mL, 6.18 mmol) in anhydrous methylene chloride at 0° C. under argon was added dropwise 2-cyanoethyl-N,N-diisopropylchlorophosphoramidite (2.15 mL, 12.36 mmol). The resulting solution was stirred at room temperature for 30 min, diluted at 0° C. with ethyl acetate, washed with cold 5% sodium bicarbonate twice, dried over sodium sulfate, and concentrated to dryness at 25° C. Chromatography on silica gel with triethylamine-ethyl acetate-hexanes (5:40:55) gave 1.25 g of the titled compound as a colorless foam, which contained two diastereomers (ratio ~1:1).

Workup

  1. washwashed with cold 5% sodium bicarbonate twice
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness at 25° C

Sources & evidence

ORD record
ord-48516b052f624ab78ab9ec07cb4fb137
Source dataset
uspto-grants-2000_07
Patent number
US06083482

Reaction notes

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