Methanesulfonic acid, 1,1,1-trifluoro-, anhydride with B,B-dibutylborinic acid → (S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-propionyl]-oxazolidin-2-one

HRID 479167

Reaction equation

HRID 479167 reaction equation
C[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][CH2:14][O:15][C:16]3[C:21]4[S:22][CH:23]=[CH:24][C:20]=4[C:19]([CH:25]=[O:26])=[CH:18][CH:17]=3)[N:12]=2)[CH:7]=1.[CH2:27]([C@H:34]1[CH2:38][O:37][C:36](=[O:39])[N:35]1[C:40](=[O:44])[CH2:41][O:42][CH3:43])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.B(OS(C(F)(F)F)(=O)=O)(CCCC)[CH2:46]CCC>>[CH2:27]([C@H:34]1[CH2:38][O:37][C:36](=[O:39])[N:35]1[C:40](=[O:44])[C@@H:41]([O:42][CH3:43])[C@H:25]([OH:26])[C:19]1[C:20]2[CH:24]=[CH:23][S:22][C:21]=2[C:16]([O:15][CH2:14][CH2:13][C:11]2[N:12]=[C:8]([C:6]3[CH:7]=[CH:2][CH:3]=[CH:4][CH:5]=3)[O:9][C:10]=2[CH3:46])=[CH:17][CH:18]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 2724243Methanesulfonic acid, 1,1,1-trifluoro-, anhydride with B,B-dibutylborinic acidHCID 10106101(S)-4-benzyl-3-(2-methoxyacetyl)oxazolidin-2-oneHCID 180036367-[2-(5-Methyl-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophene-4-carbaldehyde

Product 1

HCID 69557072(S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-propionyl]-oxazolidin-2-one

Procedure

In analogy to the procedures described in examples 11 a] to 11 c], 7-[2-(5-methyl-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophene-4-carbaldehyde was reacted with (S)-4-benzyl-3-methoxyacetyl-oxazolidin-2-one and nBu2BOTf to yield (S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-propionyl]-oxazolidin-2-one (according to NMR, one of the four isomers is strongly predominating; the configuration was tentatively assigned as 2S, 3R according to Tetrahedron Asymmetry 1999, 1353). Reduction of (S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-propionyl]-oxazolidin-2-one with triethylsilane in trifluoroacetic acid then gave (S)-4-benzyl-3-(2(S)-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-propionyl)-oxazolidin-2-one. The (S)-4-benzyl-3-(2(S)-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-propionyl)-oxazolidin-2-one was subsequently saponified with 1N NaOH in THF to yield (S)-2-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzo[b]thiophen-4-yl}-propionic acid as colorless solid.

Sources & evidence

ORD record
ord-aa595711461246fabcc17e75b62f8c1b
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Linked notes

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