Diisopropylethylamine → Tert-butyl trans-{4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl)cyclohexyl}acetate

HRID 1035699ノート

反応式

HRID 1035699 の反応式
[C:1]([O:5][C:6]([CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:24]([C:31]1[S:35][C:34]([NH2:36])=[N:33][N:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[CH2:24]([C:31]1[S:35][C:34]([NH:36][C:19]([C:18]2[CH:17]=[CH:16][C:15]([CH:12]3[CH2:13][CH2:14][CH:9]([CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH2:11]3)=[CH:23][CH:22]=2)=[O:21])=[N:33][N:32]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 7548235-Benzyl-1,3,4-thiadiazol-2-amineHCID 666854144-(4-Tert-butoxycarbonylmethylcyclohexyl)benzoic acid

生成物 1

HCID 66739902Tert-butyl trans-{4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl)cyclohexyl}acetate収率 34%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

0.45 g of 4-(4-tert-butoxycarbonylmethylcyclohexyl)benzoic acid (1.41 mmol, 1 eq.) is placed in a mixture of 5 mL of dimethylformamide at room temperature. 0.539 g of 5-benzyl-1,3,4-thiadiazol-2-amine (2.82 mmol, 2 eq.), 0.791 g of bromotris-pyrrolidinophosphonium hexafluorophosphonate (1.70 mmol, 1.2 eq.) and 0.49 mL of diisopropylethylamine (2.83 mmol, 2 eq.) are successively added. The reaction mixture is stirred for 16 hours at room temperature, diluted in ethyl acetate and washed three times with water. The organic phase is concentrated. The residue is taken up and washed with ethanol, filtered and dried. 0.236 g of tert-butyl {4-[4-(5-benzyl[1.3.4]thiadiazol-2-ylcarbamoyl)phenyl]cyclohexyl}acetate is obtained.

後処理

  1. washwashed three times with water
  2. concentrationThe organic phase is concentrated
  3. washwashed with ethanol
  4. filtrationfiltered
  5. customdried

出典と根拠

ORDレコード
ord-9f102501a5854ad1bfc91bf51fb59a82
出典データセット
uspto-grants-2013_10
特許番号
US08546391B2

反応ノート

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