Hydrochloric Acid → N-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-L-tyrosine, methyl ester

HRID 434409

反応式

HRID 434409 の反応式
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([O:15][P:16]([CH2:28][C:29]([OH:31])=O)([CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:17])[CH3:14].Cl.[CH3:33][O:34][C:35](=[O:46])[C@H:36]([CH2:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=1)[NH2:37]>C(#N)C.CO.C(N(CC)CC)C>[CH2:13]([O:15][P:16]([CH2:28][C:29]([NH:37][C@H:36]([C:35]([O:34][CH3:33])=[O:46])[CH2:38][C:39]1[CH:40]=[CH:41][C:42]([OH:45])=[CH:43][CH:44]=1)=[O:31])([CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:17])[CH3:14]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 70652Tyrosine Methyl EsterHCID 13136848[Ethoxy(4-phenylbutyl)phosphoryl]acetic acid

生成物 1

HCID 131713050N-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-L-tyrosine, methyl ester収率 88%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒HCID 8471Triethylamine溶媒

反応条件

温度
0 °C

実験手順

1,1'-Carbonyldiimidazole (0.56 g) was added portionwise to a cooled (0° C.) solution of [ethoxy(4-phenylbutyl)phosphinyl]acetic acid (0.98 g) in 70 ml of acetonitrile. This reaction mixture was stirred under argon at 0° C. for 1.5 hours. The HCl salt of L-tyrosine methyl ester (0.8 g) was dissolved in methanol and neutralized with triethylamine (0.35 g). This solution was concentrated in vacuo, dissolved in 10 ml of warm acetonitrile and added dropwise to the above solution of activated phosphinic acid ester sidechain. The reaction was stirred overnight under argon and then concentrated in vacuo. A solution of the pot residue in dichloromethane was washed (H2O, aqueous NaHCO3, brine), dried (MgSO4) and filtered to yield 1.4 g of N-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-L-tyrosine, methyl ester.

後処理

  1. concentrationThis solution was concentrated in vacuo
  2. dissolutiondissolved in 10 ml of warm acetonitrile
  3. additionadded dropwise to the above solution of activated phosphinic acid ester sidechain
  4. stirringThe reaction was stirred overnight under argon
  5. concentrationconcentrated in vacuo
  6. washA solution of the pot residue in dichloromethane was washed (H2O, aqueous NaHCO3, brine)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-37fd470cc21344d8ba7464aa0b158bd6
出典データセット
uspto-grants-1983_08
特許番号
US04396772

関連ノート

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