1-Hydroxybenzotriazole → 2-[(5-Phenyl-1,2-oxazol-3-yl)formamido]acetic acid

HRID 1093582ノート

反応式

HRID 1093582 の反応式
C1(C2ON=C(C(O)=O)C=2)C=CC=CC=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.C(OC(=O)CN)C.C([O:56][C:57](=[O:73])[CH2:58][NH:59][C:60]([C:62]1[CH:66]=[C:65]([C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[O:64][N:63]=1)=[O:61])C.O[Li].O>CN(C=O)C.O.C1COCC1.CO>[C:67]1([C:65]2[O:64][N:63]=[C:62]([C:60]([NH:59][CH2:58][C:57]([OH:73])=[O:56])=[O:61])[CH:66]=2)[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=1

参加物

12

反応物 7

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1519165-Phenyl-3-isoxazolecarboxylic acidHCID 168937Lithium hydroxide, monohydrateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 60484361[(5-Phenyl-isoxazole-3-carbonyl)-amino]-acetic acid ethyl ester

生成物 1

HCID 433543392-[(5-Phenyl-1,2-oxazol-3-yl)formamido]acetic acid収率 85.7%

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 5-phenyl-isoxazole-3-carboxylic acid (1 g, 0.00529 mol) in DMF (5 mL) was added DIPEA (2.73 g, 0.0211 mol), HOBt (0.89 g, 0.006078 mol) and EDCI.HCl (1.266 g, 0.00661 mol) at ambient temperature. After 2 minutes glycine ethyl ester hydrochloride (0.811 g, 0.00581 mol) was added and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with cold water and the resulting precipitate was isolated by filtration and dried to afford 0.744 g (56%) of 5-phenyl-isoxazole-3-carbonyl)-amino]-acetic acid ethyl ester. LCMS: 275.1 (M+1)+, 94%. To a stirred solution of [(5-phenyl-isoxazole-3-carbonyl)-amino]-acetic acid ethyl ester (0.74 g, 0.00270 mol) in a mixture of THF (5 mL), methanol (5 mL) and H2O (5 mL) was added LiOH.H2O (0.34 g, 0.00809 mol) and the resulting mixture was stirred at ambient temperature for 1 hour. Volatiles were then evaporated and the resulting residue was diluted with water and acidified with concentrated HCl. The resulting precipitate was isolated by filtration and dried to afford 0.57 g (76%) of [(5-phenyl-isoxazole-3-carbonyl)-amino]-acetic acid. LCMS: 247.06 (M+1)+, 98.18%.

後処理

  1. customthe resulting precipitate was isolated by filtration
  2. customdried
  3. customto afford 0.744 g (56%) of 5-phenyl-isoxazole-3-carbonyl)-amino]-acetic acid ethyl ester
  4. stirringthe resulting mixture was stirred at ambient temperature for 1 hour
  5. customVolatiles were then evaporated
  6. additionthe resulting residue was diluted with water
  7. customThe resulting precipitate was isolated by filtration
  8. customdried

出典と根拠

ORDレコード
ord-3c4f4604d31c45ce8e35cc238b67cd34
出典データセット
uspto-grants-2012_03
特許番号
US08129376B2

反応ノート

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