Triethylamine → 4(R)-Benzyl-3-[2-(R)-(3,4dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine-2-sulfonylmethyl)-3-methyl-butanoyl]-oxazolidin-2-one

HRID 992429Notes

Reaction equation

HRID 992429 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:24])[C@H:15]([CH2:19][S:20](Cl)(=[O:22])=[O:21])[CH:16]([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:26]1[C:31]2[S:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:30]=2[CH2:29][CH2:28][NH:27]1.C(N(CC)CC)C>ClCCl>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:24])[C@H:15]([CH2:19][S:20]([N:27]1[CH2:28][CH2:29][C:30]2[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=3[S:32][C:31]=2[CH2:26]1)(=[O:22])=[O:21])[CH:16]([CH3:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122652651,2,3,4-Tetrahydro-[1]benzothieno[2,3-c]pyridine hydrochlorideHCID 228882844-(R)-benzyl-3-(2-(R)-chlorosulfonylmethyl-3 methylbutyryl)oxazolidin-2-one

Product 1

HCID 228882824(R)-Benzyl-3-[2-(R)-(3,4dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine-2-sulfonylmethyl)-3-methyl-butanoyl]-oxazolidin-2-oneYield 34.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(R)-Benzyl-3-(2-(R)-chlorosulfonylmethyl-3-methylbutyryl)oxazolidin-2-one (370 mg) was added to a solution of 1,2,3,4-tetrahydro-benzo[4,5]thieno[2,3-c]pyridine hydrochloride (230 mg) and triethylamine (0.30 ml) in dichloromethane (20 ml) and the reaction stirred at room temperature for 18 h. The mixture was washed with water (30 ml) and brine (20 ml), dried (MgSO4), filtered and evaporated under reduced pressure to give the title compound (180 mg) in crude form.

Workup

  1. washThe mixture was washed with water (30 ml) and brine (20 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3b816fe91d44459980ea80bc91528ecc
Source dataset
uspto-grants-2002_10
Patent number
US06469020B2

Reaction notes

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