Dicyclohexylcarbodiimide → 5-(15-tert-Butoxycarbonyl-pentadecanoylamino)-isophthalic acid mono-tert-butyl ester

HRID 444986노트

반응식

HRID 444986 반응식
[C:1]([O:5][C:6](=[O:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=O)([CH3:4])([CH3:3])[CH3:2].C1C=NC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1.[C:50]([O:54][C:55](=[O:66])[C:56]1[CH:64]=[C:63]([NH2:65])[CH:62]=[C:58]([C:59]([OH:61])=[O:60])[CH:57]=1)([CH3:53])([CH3:52])[CH3:51].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:50]([O:54][C:55](=[O:66])[C:56]1[CH:64]=[C:63]([NH:65][C:21](=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:24])[CH:62]=[C:58]([C:59]([OH:61])=[O:60])[CH:57]=1)([CH3:53])([CH3:51])[CH3:52]

참가 물질

7

반응물 5

HCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 5781772316-(Tert-butoxy)-16-oxohexadecanoic acidHCID 866192463-Amino-5-(tert-butoxycarbonyl)benzoic acid

생성물 1

HCID 667245005-(15-tert-Butoxycarbonyl-pentadecanoylamino)-isophthalic acid mono-tert-butyl ester수율 86%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

To a solution of hexadecandioic acid mono t-butyl ester (100 mg, 0.29 mmol) in dry DCM (2 ml), HOAt (44 mg, 0.29 mmol) and DCC (72 mg, 32 mmol) was added. The mixture was stirred at 50° C. for 1 h. The oil bath was removed. 5-Amino-isophthalic acid mono t-butyl ester (69 mg, 0.29) and DIPEA (0.07 ml, 0.32 mmol) was added. The mixture was stirred at RT over night under nitrogen. The yellow suspension was filtered and the filtrate was concentrated. The residue was redissolved in EtOAc and extracted with 0.1N HCl (2×), brine (1×), dried (Na2SO4) and concentrated to give a white solid, which was purified twice by flash chromatography using EtOAc/Hept 1:2+5% AcOH. The title compound was obtained in 86% yield (0.140 g) as an oil containing an impurity.

후처리

  1. customThe oil bath was removed
  2. stirringThe mixture was stirred at RT over night under nitrogen
  3. filtrationThe yellow suspension was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was redissolved in EtOAc
  6. extractionextracted with 0.1N HCl (2×), brine (1×)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customto give a white solid, which
  10. customwas purified twice by flash chromatography

출처 및 근거

ORD 기록
ord-e26a64b59be544fb9b20c745a02a690a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476228B2

반응 노트

불러오는 중…