Tetrahydrofuran → HCID 86745580, compound

HRID 2372641Notes

Reaction equation

HRID 2372641 reaction equation
C1(C(C2C=CC=CC=2)NS(C)(=O)=O)C=CC=CC=1.[Cl-].[Li+].C([Li])CCC.[CH:26]1([CH2:32][C@H:33]2[C@H:37]([C:38](NCOC)=O)[O:36][C:35]([CH3:45])([CH3:44])[N:34]2[C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[C:53]1([CH:59]([C:88]2[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=2)[S:60]([NH:63]CC([C@@H]2OC(C)(C)N(C(OC(C)(C)C)=O)[C@H]2CC2CCCCC2)=O)(=[O:62])=[O:61])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.[O:94]1CCC[CH2:95]1>CCCCCC.CCOCC.CO>[C:88]1([CH:59]([C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)[S:60]([NH:63][CH:95]2[O:94][C:35]([CH3:44])([CH3:45])[N:34]([C:46]([O:48][C:49]([CH3:50])([CH3:51])[CH3:52])=[O:47])[C:33]2([C:37](=[O:36])[CH3:38])[CH2:32][CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)(=[O:62])=[O:61])[CH:93]=[CH:92][CH:91]=[CH:90][CH:89]=1

Participants

10

Reactant 6

HCID 8028TetrahydrofuranHCID 223287N-(Diphenylmethyl)methanesulfonamideHCID 433294Lithium ChlorideHCID 57288628HCID 57288628, compoundHCID 86745581HCID 86745581, compoundHCID 178418339Butyllithium

Product 1

HCID 86745580HCID 86745580, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

N-(Diphenylmethyl)methanesulfonamide (6.34 g., 19.5 mmole, 2.5 eq.) and lithium chloride (1.65 g., 39 mmole, 5 eq.) were partially dissolved in distilled tetrahydrofuran (78 ml., 0.25M) and cooled to -40° . n-Butyllithium (2.5M in hexane, 15.6 ml., 39 mmole, 5 eq.) was added slowly. The mixture was stirred at -40° for 30 minutes and then warmed to 0° for 30 minutes. After recooling to -40° , (4S-trans)-4-(cyclohexylmethyl)-5-[[(methoxy)methylamino]carbonyl]-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester [3.0 g., 7.8 mmole, 1 eq., prepared as described in Example 1(b)] was added. The reaction was stirred at -40° for 30 minutes and at 0° for 30 minutes, then quenched with 1N HCl (50 ml.). The product was extracted into ether (3×75 ml.), dried (Na2SO 4 and MgSO4), and freed of solvent in vacuo. The product was purified by chromatography on silica gel (270 g. Merck) eluting with ether:hexane (1:3) followed by (1:2) to give 4.45 g. of (4S-trans)-5-[[[(diphenylmethyl)sulfonyl]-amino]acetyl]-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester; [α]D =+30.3° (c=1.0, methanol). TLC (silica gel; ether:hexane, 1:1) Rf =0.56.

Workup

  1. temperaturecooled to -40°
  2. temperaturewarmed to 0° for 30 minutes
  3. customAfter recooling to -40°
  4. stirringThe reaction was stirred at -40° for 30 minutes and at 0° for 30 minutes
  5. customquenched with 1N HCl (50 ml.)
  6. extractionThe product was extracted into ether (3×75 ml.)
  7. dry with materialdried (Na2SO 4 and MgSO4)
  8. customThe product was purified by chromatography on silica gel (270 g. Merck)
  9. washeluting with ether:hexane (1:3)
  10. customto give 4.45 g

Sources & evidence

ORD record
ord-65072c42e8324ff2977a474ab21b1e58
Source dataset
uspto-grants-1992_03
Patent number
US05098924

Reaction notes

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