Methyl 5-(2-(tert-butoxycarbonylamino)acetamido)-2-hydroxybenzoate → Methyl 5-(2-aminoacetamido)-2-hydroxybenzoate

HRID 1026877ノート

反応式

HRID 1026877 の反応式
C(OC([NH:8][CH2:9][C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:11])=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:8][CH2:9][C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:11]

参加物

4

反応物 1

HCID 67174569Methyl 5-(2-(tert-butoxycarbonylamino)acetamido)-2-hydroxybenzoate

生成物 1

HCID 59193335Methyl 5-(2-aminoacetamido)-2-hydroxybenzoate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

The methyl 5-(2-(tert-butoxycarbonylamino)acetamido)-2-hydroxybenzoate (1.3 g, 4.0 mmol) was dissolved in CH2Cl2 (15 mL) and TFA (8 mL). The reaction was stirred (RT, 2.5 h) and then concentrated to afford methyl 5-(2-aminoacetamido)-2-hydroxybenzoate as a clear oil. [M+H]+=225.1. The oil was dissolved in CH2Cl2 (20 mL) and to this was added DHA (1.3 g, 4.0 mmol), EDCI (0.84 g, 4.4 mmol) and triethylamine (2.0 g, 20.0 mmol). The reaction was stirred (RT, 4 h) and then partitioned between CH2Cl2 and brine. The aqueous layer was extracted with CH2Cl2, and the combined organic layers were dried over MgSO4. The crude material was purified by silica chromatography (0-5% MeOH/CH2Cl2) to afford 0.9 g of methyl 5-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoacetamido)-2-hydroxybenzoate as a tan solid. Mass calculated for C10H12N2O4=534.69. found: [M+H]+=535.4.

後処理

  1. concentrationconcentrated

出典と根拠

ORDレコード
ord-3e7c62e78147475a9bebc2a70f32279c
出典データセット
uspto-grants-2014_05
特許番号
US08729293B2

反応ノート

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