Tetrahydrofuran → HCID 59849018, compound

HRID 2237729Notes

Reaction equation

HRID 2237729 reaction equation
[I-].C[S+](C)(C)=O.[CH3:7]C(C)([O-])C.[K+].O1CCCC1.[CH:18]([C@@H:20]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])[CH2:21][C@H:22]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH2:36][CH2:37][CH2:38][O:39][CH3:40])[CH:28]=1)[CH:23]([CH3:25])[CH3:24])=[O:19]>CS(C)=O>[CH3:34][O:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][C@H:22]([CH:23]([CH3:24])[CH3:25])[CH2:21][C@H:20]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:46])([CH3:45])[CH3:47])[C@@H:18]2[CH2:7][O:19]2)=[CH:28][C:29]=1[O:35][CH2:36][CH2:37][CH2:38][O:39][CH3:40]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 11590225tert-Butyl [(2S,4S)-4-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-5-methyl-1-oxohexan-2-yl]carbamateHCID 23665647Potassium tert-butoxide

Product 1

HCID 59849018HCID 59849018, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

3.87 g of trimethylsulphoxonium iodide and 1.98 g of potassium tert-butoxide are stirred under high vacuum overnight, admixed with 24 ml of tetrahydrofuran and subsequently cooled to 0° C. A solution of 4.00 g of tert-butyl {1(S)-formyl-3(S)-[4-methoxy-3-(3-methoxypropoxy)benzyl]4-methylpentyl}carbamate [CAS 172900-83-3] in 24 ml of dimethyl sulphoxide is added dropwise. After 2 hours, the reaction mixture is partitioned between water and tert-butyl methyl ether and the aqueous phase is extracted once more with tert-butyl methyl ether (2×). The combined organic phases are washed successively with water (3×) and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue first by means of flash chromatography (SiO2 60F) and then by means of crystallization (hexane) as white crystals. Rf=0.43 (1:1 EtOAc-heptane); Rt=21.90 (gradient II); m.p. 59-65° C.

Workup

  1. customthe reaction mixture is partitioned between water and tert-butyl methyl ether
  2. extractionthe aqueous phase is extracted once more with tert-butyl methyl ether (2×)
  3. washThe combined organic phases are washed successively with water (3×) and brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-fc340f185e8d4b2686f11227350aaf58
Source dataset
uspto-grants-2010_05
Patent number
US07718675B2

Reaction notes

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