Phthalic Anhydride → (2S)3-Benzyloxycarbonylamino-2-phthalimidopropionic acid

HRID 1643376ノート

反応式

HRID 1643376 の反応式
C1(NC2CCCCC2)CCCCC1.[CH2:14]([O:21][C:22]([NH:24][CH2:25][C@H:26]([NH:30][C:31]([O:33]C(C)(C)C)=O)[C:27]([OH:29])=[O:28])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(=O)O[C:41](=[O:42])[C:40]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:39]12>ClCCl.Cl.C1(C)C=CC=CC=1>[CH2:14]([O:21][C:22]([NH:24][CH2:25][C@H:26]([N:30]1[C:31](=[O:33])[C:39]2=[CH:47][CH:46]=[CH:45][CH:44]=[C:40]2[C:41]1=[O:42])[C:27]([OH:29])=[O:28])=[O:23])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

6

反応物 2

HCID 6811Phthalic AnhydrideHCID 2755949Boc-Dap(Z)-OH.DCHA

生成物 1

HCID 18396554(2S)3-Benzyloxycarbonylamino-2-phthalimidopropionic acid

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A solution of (2S)3-benzyloxycarbonylamino-2-tert-butoxycarbonylaminopropionic acid dicyclohexylamine salt (3 g, 5.8 mmol) in dichloromethane (200 ml) was washed four times with 1M HCl solution, dried (MgSO4) and concentrated. The resulting oil was dissolved in dry dichloromethane (35 ml), cooled to 0° C. and treated with trifluoroacetic acid (35 ml). This solution was stirred at 0° C. for 1.5 h then evaporated to dryness. Dichloromethane (50 ml) was added to the residue then removed under vacuum. This process repeated six times to afford a white solid. The white solid was suspended in toluene (50 ml), treated with powdered phthalic anhydride (940 mg, 6.35 mmol) and refluxed for 18 h. The resulting solution was concentrated to afford an oil which was purified by flash chromatography (2-10% methanol/dichloromethane) to afford 266, 2.01 g (94%) as a white powder: IR (KBr) 3600-2500br, 1776, 1714, 1530, 1469, 1455, 1392, 1263, 1131, 722; 1H NMR (CDCl3) δ 7.83 (2H, m), 7.72 (2H, m), 7.29 (5H, m), 5.41 (1H, m), 5.03 (2H, s), 3.90 (2H, m); MS (ES−), 367 (M−1).

後処理

  1. dry with materialdried (MgSO4)
  2. concentrationconcentrated
  3. dissolutionThe resulting oil was dissolved in dry dichloromethane (35 ml)
  4. additiontreated with trifluoroacetic acid (35 ml)
  5. customthen evaporated to dryness
  6. additionDichloromethane (50 ml) was added to the residue
  7. customthen removed under vacuum
  8. customto afford a white solid
  9. temperaturerefluxed for 18 h
  10. concentrationThe resulting solution was concentrated
  11. customto afford an oil which
  12. customwas purified by flash chromatography (2-10% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-d8a4c96bb4e84996974e5ca7963bcd8a
出典データセット
uspto-grants-2012_02
特許番号
US08119631B2

反応ノート

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