Triethylsilane → (S)-2-methoxy-3-(7-(2-(5-methyl-2-phenyloxazol-4-yl)ethoxy)benzo[b]thiophen-4-yl)propanoic acid

HRID 479168Notes

Reaction equation

HRID 479168 reaction equation
C([O:3][C@@H](CC1C=CC(OCCC2N=C(C3C=CC=CC=3)OC=2C)=C(OC)C=1)C(O)=O)C.C([C@H]1COC(=O)N1[C:45](=[O:75])[C@@H:46]([O:73][CH3:74])[C@H:47](O)[C:48]1[C:56]2[CH:55]=[CH:54][S:53][C:52]=2[C:51]([O:57][CH2:58][CH2:59][C:60]2[N:61]=[C:62]([C:66]3[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=3)[O:63][C:64]=2[CH3:65])=[CH:50][CH:49]=1)C1C=CC=CC=1.C([SiH](CC)CC)C.C([C@H]1COC(=O)N1C(=O)[C@@H](OC)CC1C2C=CSC=2C(OCCC2N=C(C3C=CC=CC=3)OC=2C)=CC=1)C1C=CC=CC=1.[OH-].[Na+]>FC(F)(F)C(O)=O.C1COCC1>[CH3:74][O:73][C@@H:46]([CH2:47][C:48]1[C:56]2[CH:55]=[CH:54][S:53][C:52]=2[C:51]([O:57][CH2:58][CH2:59][C:60]2[N:61]=[C:62]([C:66]3[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=3)[O:63][C:64]=2[CH3:65])=[CH:50][CH:49]=1)[C:45]([OH:75])=[O:3]

Participants

8

Reactant 5

HCID 12052TriethylsilaneHCID 14798Sodium HydroxideHCID 10273971(2S)-2-Ethoxy-3-{3-methoxy-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acidHCID 20599097(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-oneHCID 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-one2×

Product 1

HCID 44591815(S)-2-methoxy-3-(7-(2-(5-methyl-2-phenyloxazol-4-yl)ethoxy)benzo[b]thiophen-4-yl)propanoic acid

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent

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-7d28276cdcc246be9ff52fc10a737c83
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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