Water → HCID 86613537, compound

HRID 2237739Notes

Reaction equation

HRID 2237739 reaction equation
[Si]([O:8][C@H:9]([C@@H:18]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:19][C@H:20]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])[CH:26]=1)[CH:21]([CH3:23])[CH3:22])[CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:17])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[OH:8][C@H:9]([C@@H:18]([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:43])([CH3:45])[CH3:44])[CH2:19][C@H:20]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])[CH:26]=1)[CH:21]([CH3:23])[CH3:22])[CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][NH:13][C:12]1=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 86613538HCID 86613538, compound

Product 1

HCID 86613537HCID 86613537, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of 0.035 g of tert-butyl {1(S)-[1(S)-(tert-butyldimethylsilanyloxy)-2-(2-oxotetrahydropyrimidin-1-yl)ethyl]-3(S)-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate in 0.65 ml of tetrahydrofuran is admixed with 0.064 ml of 1M tetrabutylammonium fluoride (in tetrahydrofuran) and stirred at room temperature over 18 hours. The reaction solution is admixed with water and extracted with tert-butyl methyl ether (2×). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a colourless oil. Rf=0.36 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=4.44 (gradient I).

Workup

  1. extractionextracted with tert-butyl methyl ether (2×)
  2. washThe combined organic phases are washed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-d5b9863c4ec94294887f559c3b7585a3
Source dataset
uspto-grants-2010_05
Patent number
US07718675B2

Reaction notes

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