참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Triphenylphosphine | HCID 11776 | — |
| 반응물 | 4-(Benzyloxy)-3-methoxybenzaldehyde | HCID 75506 | — |
| 반응물 | ethyl N-ethoxycarbonyliminocarbamate | HCID 220568 | — |
| 반응물 | Ethyl isopropoxyacetate | HCID 537908 | — |
| 반응물 | 3,5-Dimethoxythiobenzamide | HCID 2758491 | — |
| 반응물 | Methyl 4-bromo-3-oxopentanoate | HCID 9815681 | — |
| 반응물 | 2-[2-(3,5-Dimethoxy-phenyl)-5-methyl-thiazol-4-yl)-ethanol | HCID 22647453 | — |
| 반응물 | [Rac]-3-(4-hydroxy-3-methoxy-phenyl)-2-isopropoxy-propionic acid ethyl ester | HCID 68616023 | — |
| 용매 | Tetrahydrofuran | HCID 8028 | — |
| 생성물 | HCID 68616500 | HCID 68616500 | — |
반응 단계
In analogy to the procedure described in example 1 d], [rac]-3-(4-hydroxy-3-methoxy-phenyl)-2-isopropoxy-propionic acid ethyl ester [prepared from isopropoxy-acetic acid ethyl ester (Tetrahedron (1982), 38(17), 2733-9) and 4-benzyloxy-3-methoxy-benzaldehyde in analogy to the procedures described in examples 54 a]to c)] was reacted with 2-[2-(3,5-dimethoxy-phenyl)-5-methyl-thiazol-4-yl]-ethanol (prepared from [rac]-4-bromo-3-oxo-pentanoic acid methyl ester [PCT Int. Appl. (2001), WO 01/79202] and 3,5-dimethoxy-thiobenzamide [PCT Int. Appl. (1992), WO 92/09586 A1] in analogy to the procedures described in examples 12 a] and 12 b]) in tetrahydrofuran in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]-3-(4-{2-[2-(3,5-dimethoxy-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3-methoxy-phenyl)-2-isopropoxy-propionic acid ethyl ester, which was further saponified in analogy to the procedure described in example 4 e], to yield [rac]-3-(4-{2-[2-(3,5-dimethoxy-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3-methoxy-phenyl)-2-isopropoxy-propionic acid as colorless solid.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 특허 번호 | US06809110B2 |
|---|
| 출처 데이터셋 | uspto-grants-2004_10 |
|---|
| ORD ID | ord-a2edefffac9f4853ab6615e274df37f6 |
|---|
| 출처 메모 | uspto-grants-2004_10 |
|---|