Triethylsilane → (S)-2-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-in dan-4-yl}-propionic acid

HRID 479170Notes

Reaction equation

HRID 479170 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)N1C(=O)[C@@H](OC)[C@H](O)C1C=CC(OCCC2N=C(C3C=CC=CC=3)OC=2C)=C2C=1CCC2)C1C=CC=CC=1.C([SiH](CC)CC)C.C([C@H]1COC(=O)N1[C:96](=[O:125])[C@@H:97]([O:123][CH3:124])[CH2:98][C:99]1[CH:107]=[CH:106][C:105]([O:108][CH2:109][CH2:110][C:111]2[N:112]=[C:113]([C:117]3[CH:122]=[CH:121][CH:120]=[CH:119][CH:118]=3)[O:114][C:115]=2[CH3:116])=[C:104]2[C:100]=1[CH2:101][CH2:102][CH2:103]2)C1C=CC=CC=1.[OH-].[Na+]>FC(F)(F)C(O)=O.C1COCC1>[CH3:124][O:123][C@@H:97]([CH2:98][C:99]1[CH:107]=[CH:106][C:105]([O:108][CH2:109][CH2:110][C:111]2[N:112]=[C:113]([C:117]3[CH:122]=[CH:121][CH:120]=[CH:119][CH:118]=3)[O:114][C:115]=2[CH3:116])=[C:104]2[C:100]=1[CH2:101][CH2:102][CH2:103]2)[C:96]([OH:3])=[O:125]

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 20599098(S)-4-benzyl-3-(2(S)-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-propionyl)-oxazolidin-2-one2×HCID 69557192(S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-propionyl]oxazolidin-2-one

Product 1

HCID 69557438(S)-2-methoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-in dan-4-yl}-propionic 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-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-carbaldehyde (example 91 b]) 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[-indan-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]-indan-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]-indan-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]-indan-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]-in dan-4-yl}-propionic acid as colorless solid after crystallization from AcOEt/hexane. The enantiomeric excess was judged according to chiral HPLC (Chiralpak-AD) to be 97.7%.

Sources & evidence

ORD record
ord-4635cc7b9e354cc48c367e0434730087
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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