Triphenylphosphine → 3-[3-Tert-butoxycarbonyl-4(S)-(4-iodo-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide

HRID 863218Notes

Reaction equation

HRID 863218 reaction equation
[I:1]NC(=O)CCC(N)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:29]([NH:33][C:34](=[O:59])[C@H:35]([CH3:58])[CH2:36][C@@H:37]1[O:41][C:40]([CH3:43])([CH3:42])[N:39]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C@H:38]1[CH2:51][C:52]([CH3:57])([CH3:56])[CH2:53][CH2:54]O)[CH2:30][CH2:31][CH3:32]>C(Cl)Cl>[CH2:29]([NH:33][C:34](=[O:59])[C@H:35]([CH3:58])[CH2:36][C@@H:37]1[O:41][C:40]([CH3:43])([CH3:42])[N:39]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C@H:38]1[CH2:51][C:52]([CH3:57])([CH3:56])[CH2:53][CH2:54][I:1])[CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 21864724N-IodosuccinamideHCID 867520963-[3-tert-butoxycarbonyl-4(S)-(4-hydroxy-2,2-dimethylbutyl)-2,2-dimethyloxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide

Product 1

HCID 867520973-[3-Tert-butoxycarbonyl-4(S)-(4-iodo-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

168 mg of N-iodosuccinamide and 196 mg of triphenylphosphine are added to a solution of 300 mg of 3-[3-tert-butoxycarbonyl-4(S)-(4-hydroxy-2,2-dimethylbutyl)-2,2-dimethyl-1,3-oxazolidin-5(S)-yl]-2(R)-methyl-propionic acid (N-butyl)amide (Example 1c)) in 5 ml of methylene chloride at 0° C. and the reaction mixture is stirred for 7 h. The crude product is purified, after customary working up, over 65 g of silica gel (mobile phase B) to give the title compound: Rf (B)=0.55.

Workup

  1. customThe crude product is purified

Sources & evidence

ORD record
ord-df46d8c5aab348e7b35b553123cb01f5
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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