Ammonium Hydroxide → Cdc-801

HRID 2348

반응식

HRID 2348 반응식
[C:1]1(=[O:30])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:12]=2)[CH2:7][C:8](O)=[O:9])[C:4](=[O:25])[C:3]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:2]12.C(N1C=CN=C1)([N:33]1C=CN=C1)=O.[OH-].[NH4+]>CN(C)C1C=CN=CC=1.O1CCCC1>[C:1]1(=[O:30])[N:5]([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[CH:12]=2)[CH2:7][C:8]([NH2:33])=[O:9])[C:4](=[O:25])[C:3]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:2]12

참가 물질

6

반응물 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 98016133-(3-Cyclopentyloxy-4-methoxyphenyl)-3-phthalimidopropanoic acid

생성물 1

HCID 9844338Cdc-801수율 62.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

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온도
25 °C

실험 절차

A mixture of 3-phthalimido-3-(3-cyclopentyloxy-4-methoxyphenyl)propionic acid (2.05 g, 5.00 mmol), 1,1'-carbonyldiimidazole (0.91 g, 5.5 mmol) and 4-dimethylaminopyridine (trace) in tetrahydrofuran (20 mL) was stirred for 1.5 hours under nitrogen at approximately 25° C. To the solution was added ammonium hydroxide (1.07 mL, 16.0 mmol, 28-30%) and stirring was continued for 1.5 hours. A small amount of solid forms during this time. The mixture was concentrated to half its volume and a white solid precipitated. The mixture was filtered, washed with a small amount of tetrahydrofuran, air dried, and dried in vacuo (60° C.,<1 mm) to afford 1.27 g of the product. The product was further purified by flash column chromatography (silica gel, 5% methanol/methylene chloride) and the resulting white solid was dried in vacuo (60° C., <1 mm) to afford 1 g (49%) of the product: mp 165°-166° C.; 1H NMR (CDCl3) δ 7.85-7.61 (m, 4H), 7.16-7.04 (m, 2H), 6.85-6.75 (m, 1H), 5.80 (dd, J=5.8, 10.4 Hz, 1H), 5.66 (br s, 1H), 5.54 (br s, 1H), 4.82-4.70 (m, 1H), 3.80 (s, 3H), 3.71 (dd, J=10.4, 15 Hz, 1H), 3.06 (dd, J=5.8, 15 Hz, 1H), 2.06-1.51 (m, 8H); 13C NMR (CDCl3) δ 171.8, 168.3, 149.8, 147.7, 133.9, 131.8, 131.3, 123.3, 119.9, 114.6, 111.8, 80.4, 56.0, 51.6, 37.9, 32.7, 24.1; Anal. Calcd for C23 H24N2O5. Theoretical: C, 67.63; H, 5.92; N, 6.86. Found: C, 67.25; H, 5.76; N, 6.68.

후처리

  1. stirringstirring
  2. waitwas continued for 1.5 hours
  3. concentrationThe mixture was concentrated to half its volume
  4. customa white solid precipitated
  5. filtrationThe mixture was filtered
  6. washwashed with a small amount of tetrahydrofuran, air
  7. customdried
  8. customdried in vacuo (60° C.,<1 mm)

출처 및 근거

ORD 기록
ord-f310c91312a24ed185ed64c535694b9b
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728844

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