L-Proline → 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,2,4-thiadiazol-3-yl}-2-ethylphenyl)ethyl]-L-proline

HRID 1942758ノート

反応式

HRID 1942758 の反応式
[CH2:1]([C:3]1[C:8]([CH2:9][CH:10]=O)=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[N:16]=[C:15]([C:17]2[CH:18]=[CH:19][C:20]([CH2:25][CH:26]([CH3:28])[CH3:27])=[C:21]([CH:24]=2)[C:22]#[N:23])[S:14][N:13]=1)[CH3:2].[NH:29]1[CH2:36][CH2:35][CH2:34][C@H:30]1[C:31]([OH:33])=[O:32].C([BH3-])#N.[Na+]>C(O)C>[C:22]([C:21]1[CH:24]=[C:17]([C:15]2[S:14][N:13]=[C:12]([C:4]3[C:3]([CH2:1][CH3:2])=[C:8]([CH2:9][CH2:10][N:29]4[CH2:36][CH2:35][CH2:34][C@H:30]4[C:31]([OH:33])=[O:32])[CH:7]=[CH:6][CH:5]=3)[N:16]=2)[CH:18]=[CH:19][C:20]=1[CH2:25][CH:26]([CH3:28])[CH3:27])#[N:23]

参加物

5

反応物 3

HCID 145742L-ProlineHCID 5003444Sodium cyanoborohydrideHCID 58494132HCID 58494132、化合物

生成物 1

HCID 545784641-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,2,4-thiadiazol-3-yl}-2-ethylphenyl)ethyl]-L-proline収率 15.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 5-{3-[2-ethyl-3-(2-oxoethyl)phenyl]-1,2,4-thiadiazol-5-yl}-2-(2-methylpropyl)benzonitrile (D62) (100 mg, 0.257 mmol) and L-proline (59.1 mg, 0.513 mmol) stirred in Ethanol (10 mL) for 20 min was added sodium cyanoborohydride (48.4 mg, 0.770 mmol). This mixture was stirred at room temperature for 2 h. The reaction was quenched with water, then dried and dissolved in DMF. The residue was purified by for Mass Directed AutoPrep to afford 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,2,4-thiadiazol-3-yl}-2-ethylphenyl)ethyl]-L-proline (E76) (20 mg) as a TFA salt (white solid).

後処理

  1. customThe reaction was quenched with water
  2. customdried
  3. dissolutiondissolved in DMF
  4. customThe residue was purified by for Mass Directed AutoPrep

出典と根拠

ORDレコード
ord-f43a625880cc48a1b46503d94fa27b9e
出典データセット
uspto-grants-2013_03
特許番号
US08389508B2

反応ノート

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