L-Tyrosine 1,1-dimethylethyl ester → tert-butyl (2S)-2-[[4-(dihexylamino)-1,1-dioxo-1,2,5-thiadiazol-3-yl]amino]-3-(4-hydroxyphenyl)propanoate

HRID 1070444

반응식

HRID 1070444 반응식
[CH2:1]([N:7]([C:14]1[C:15](OCC)=[N:16][S:17](=[O:20])(=[O:19])[N:18]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:24]([O:28][C:29](=[O:40])[C@H:30]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[NH2:31])([CH3:27])([CH3:26])[CH3:25]>CCO>[C:24]([O:28][C:29](=[O:40])[C@H:30]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1)[NH:31][C:15]1[C:14]([N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[N:18][S:17](=[O:19])(=[O:20])[N:16]=1)([CH3:27])([CH3:25])[CH3:26]

참가 물질

4

반응물 2

HCID 6950582L-Tyrosine 1,1-dimethylethyl esterHCID 221387874-(N,N-di-n-hexylamino)-3-ethoxy-1,1-dioxo-1,2,5-thiadiazole

생성물 1

HCID 178444783tert-butyl (2S)-2-[[4-(dihexylamino)-1,1-dioxo-1,2,5-thiadiazol-3-yl]amino]-3-(4-hydroxyphenyl)propanoate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 4-(N,N-di-n-hexylamino)-3-ethoxy-1,1-dioxo-1,2,5-thiadiazole (400 mg, 1.02 mmol) and L-tyrosine t-butyl ester (261 mg, 1.1 mmol) in EtOH (10 mL) was stirred at room temperature for 36 hrs. The solvent was removed under reduced pressure residue purified by flash column chromatography (silica, hexane:EtOAc 3:1 then 1:1) to give N-(4-(N,N-di-n-hexylamino)-1,1-dioxo-1,2,5-thiadiazol-3-yl)-L-tyrosine tert-butyl ester as a white waxy solid (400 mg, 73%). Anal. Calc'd for C27H44N4O5 S.0.55EtOAc: C, 59.93; H, 8.34; N, 9.57. Found: C,59.84; H, 8.44; N,9.62.

후처리

  1. customThe solvent was removed under reduced pressure residue
  2. custompurified by flash column chromatography (silica, hexane:EtOAc 3:1

출처 및 근거

ORD 기록
ord-a0361812ef8f4af7aa3916bb6088253d
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903088B2

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