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Trifluoroacetic acid → 2-(7-(Leucinyl)aminonaphtho[2,1-d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

HRID 64517
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인쇄 미리보기

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HRID 64517 반응식
C([NH:8][C@H:9]([C:14]([NH:16][C:17]1[CH:18]=[C:19]2[C:27](=[CH:28][CH:29]=1)[C:26]1[S:25][C:24]([C:30]#N)=[N:23][C:22]=1[CH:21]=[CH:20]2)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])(OC(C)(C)C)=O.C1(SC)C=CC=CC=1.FC(F)(F)C(O)=O.O.Cl.[NH2:49][C@@H:50]([C:53]([OH:55])=[O:54])[CH2:51][SH:52].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[NH2:8][C@H:9]([C:14]([NH:16][C:17]1[CH:18]=[C:19]2[C:27](=[CH:28][CH:29]=1)[C:26]1[S:25][C:24]([C:30]3[S:52][CH2:51][CH:50]([C:53]([OH:55])=[O:54])[N:49]=3)=[N:23][C:22]=1[CH:21]=[CH:20]2)=[O:15])[CH2:10][CH:11]([CH3:12])[CH3:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 5

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 11430Potassium CarbonateHCID 10176341D-Cysteine hydrochloride monohydrateHCID 1176049817-(Boc-leucinyl)aminonaphtho[2,1-d]thiazole-2-carbonitrile

생성물 1

HCID 1176045022-(7-(Leucinyl)aminonaphtho[2,1-d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

7-(Boc-leucinyl)aminonaphtho[2,1-d]thiazole-2-carbonitrile (69 mg, 0.16 mmol) was combined with 0.5 mL of thioanisole and 1.5 mL of DCM and stirred in an ice bath. Trifluoroacetic acid (1.5 mL) was added, and the reaction monitored by HPLC. After 1 h, solvents were removed under reduced pressure, and the remaining residue triturated with ether. The resulting solid was taken up in MeCN/H2O and treated with D-cysteine hydrochloride hydrate (55 mg, 0.31 mmol) and potassium carbonate (55 mg, 0.40 mmol). After 20 min, the reaction was filtered and the product was isolated by preparative HPLC eluting with 2→50% MeCN in 0.1% formic acid. Calcd for C21H23N4O3S2 (M+H): 443.1. found 443.

후처리

  1. customsolvents were removed under reduced pressure
  2. customthe remaining residue triturated with ether
  3. waitAfter 20 min
  4. filtrationthe reaction was filtered
  5. customthe product was isolated by preparative HPLC
  6. washeluting with 2→50% MeCN in 0.1% formic acid

출처 및 근거

ORD 기록
ord-3f81971b3c1a40db94d050ff4c49361c
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09447450B2

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