Triethylamine → (S)-2-[[[1-[[(S)-2-[[(1,1,-Dimethylethoxy)carbonyl]amino]-1-oxohexyl]amino]pentyl]methoxyphosphinyl]oxy-1-oxopropyl]-L-proline, ethyl ester

HRID 231944

反応式

HRID 231944 の反応式
C(N(CC)CC)C.[C:8](Cl)(=[O:13])[C:9](C)(C)[CH3:10].NC(P(OC)(O[C@@H](C)C([N:27]1[CH2:36][CH2:35][CH2:34][C@H:28]1[C:29]([O:31][CH2:32][CH3:33])=[O:30])=O)=O)CCCC.FC(F)(F)C(NCCCC[C@H](OP(C(NC(OCC1C=CC=CC=1)=O)CCCC)(OC)=O)C(N1CCC[C@H]1C(OCC)=O)=O)=O.[CH3:85][C:86]([CH3:124])([O:88][C:89]([NH:91][C@@H:92]([CH2:120][CH2:121][CH2:122][CH3:123])[C:93]([NH:95][CH:96]([P:101]([O:118][CH3:119])([O:103][C@@H](C)C(N1CCC[C@H]1C(OCC)=O)=O)=[O:102])[CH2:97][CH2:98][CH2:99][CH3:100])=[O:94])=[O:90])[CH3:87]>O1CCCC1.C(O)(=O)C.CO.C(Cl)Cl>[CH3:85][C:86]([CH3:87])([O:88][C:89]([NH:91][C@@H:92]([CH2:120][CH2:121][CH2:122][CH3:123])[C:93]([NH:95][CH:96]([P:101]([O:118][CH3:119])([O:103][CH2:10][CH2:9][C:8]([C@:28]1([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:34][CH2:35][CH2:36][NH:27]1)=[O:13])=[O:102])[CH2:97][CH2:98][CH2:99][CH3:100])=[O:94])=[O:90])[CH3:124]

参加物

10

反応物 5

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 1317160041-[(S)-6-[(Trifluoroacetyl)amino]-2-[[[1-[[(phenylmethoxy)carbonyl]amino]pentyl]methoxyphosphinyl]oxy]-1-oxohexyl]-L-proline, ethyl esterHCID 1317160081-[(S)-2-[[[(1-amino)pentyl]methoxyphosphinyl]oxy]-1-oxopropyl]-L-proline, ethyl esterHCID 1317160091-[(S)-2-[[[1-[[(S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxohexyl]amino]pentyl]methoxyphosphinyl]oxy]-1-oxopropyl]-L-proline, ethyl ester

生成物 1

HCID 131716007(S)-2-[[[1-[[(S)-2-[[(1,1,-Dimethylethoxy)carbonyl]amino]-1-oxohexyl]amino]pentyl]methoxyphosphinyl]oxy-1-oxopropyl]-L-proline, ethyl ester

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

N-[(1,1-Demethylethoxy)carbonyl]-L-norleucine (432 mg., 1.87 mmole) is dissolved in tetrahydrofuran (10 ml.) at room temperature under argon. The mixture is cooled to 0° and treated with triethylamine (0.66 ml., 4.56 mmole) and pivaloyl chloride (0.28 ml.). After one hour at 0°, the reaction mixture is treated with a solution of 1-[(S)-2-[[[(1-amino)pentyl]methoxyphosphinyl]oxy]-1-oxopropyl]-L-proline, ethyl ester (isomer B) (706 mg., 1.87 mmole) in tetrahydrofuran (10 ml.) according to the procedure of Example 4 part (e) to give 759 mg. of 1-[(S)-2-[[[1-[[(S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-oxohexyl]amino]pentyl]methoxyphosphinyl]oxy]-1-oxopropyl]-L-proline, ethyl ester (isomer B). TLC (silica gel; methylene chloride:methanol:acetic acid, 20:1:1) Rf =0.74.

後処理

  1. temperatureThe mixture is cooled to 0°
  2. customto give 759 mg

出典と根拠

ORDレコード
ord-1b9951ea3186438d81b1b0801d1304a6
出典データセット
uspto-grants-1989_07
特許番号
US04849414

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