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

HRID 64517
ノート
印刷プレビュー

反応式

HRID 64517 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3f81971b3c1a40db94d050ff4c49361c
出典データセット
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09447450B2

反応ノート

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