Oxalyl chloride → HCID 22905326, 화합물

HRID 865348노트

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HRID 865348 반응식
C(Cl)(=O)C(Cl)=O.[C:7]([C:9]1[CH:28]=[CH:27][C:12]([CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]([N+:24]([O-:26])=[O:25])=[C:19]([CH:23]=2)[C:20]([OH:22])=O)=[CH:11][CH:10]=1)#[N:8].Cl.[CH2:30]([O:32][C:33](=[O:37])[CH2:34][CH2:35][NH2:36])[CH3:31].C(=O)(O)[O-].[Na+]>C1C=CC=CC=1.O1CCCC1.O.CN(C)C=O>[CH2:30]([O:32][C:33](=[O:37])[CH2:34][CH2:35][NH:36][C:20](=[O:22])[C:19]1[CH:23]=[C:15]([O:14][CH2:13][C:12]2[CH:11]=[CH:10][C:9]([C:7]#[N:8])=[CH:28][CH:27]=2)[CH:16]=[CH:17][C:18]=1[N+:24]([O-:26])=[O:25])[CH3:31]

참가 물질

8

반응물 4

HCID 65578Oxalyl chlorideHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 516892Sodium BicarbonateHCID 229049555-(4-Cyanobenzyloxy)-2-nitrobenzoic acid

생성물 1

HCID 22905326HCID 22905326, 화합물수율 91.1%

시약·촉매·용매 3

HCID 241Benzene용매HCID 6228Dimethylformamide용매HCID 21881883Oxolane--water (1/1)용매

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온도
60 °C

실험 절차

Oxalyl chloride (5.70 mL, 65.4 mmol) was added slowly to a rapidly stirred suspension of 14.6 g (48.9 mmol) of 5-(4-cyanobenzyloxy)-2-nitrobenzoic acid and 2 mL of dimethylformamide in 100 mL of benzene. When gas evolution ceased, the solution was heated briefly to 60° C., concentrated in vacuo, and redissolved in 75 mL of tetrahydrofuran. This solution was added dropwise to a rapidly stirred suspension of 8.50 g (55.3 mmol) of b-alanine ethyl ester hydrochloride and 21.1 g (251 mmol) of sodium bicarbonate in 325 mL of 2:1 tetrahydrofuran/water at 0° C. The mixture was warmed to ambient temperature for 12 h and the tetrahydrofuran was removed in vacuo. The residue was partitioned between ethyl acetate and 1N sodium bicarbamate and the aqueous phase was separated and extracted with ethyl acetate. The combined organics were washed with 1N sodium hydrogen sulfate, water, brine, dried over anhydrous magnesium sulfate, and concentrated to give 17.7 g (91%) of N-(5-(4-cyanobenzyloxy)-2-nitrobenzoyl)-b-alanine ethyl ester as a tan powder. 1H NMR (300 MHz, CDCl3) d 8.11 (1H, d, J=8.3 Hz, O-Ar-H), 7.71 (2H, d, J=8.3 Hz, NC-Ar-H2), 7.52 (2H, d, J=8.3 Hz, NC-Ar-H2), 7.01 (2H, m, O-Ar-H2), 6.50 (1H, bt, J=5.9 Hz, N-H), 5.21 (2H, s, ArCH2O), 4.14 (2H, q, J=7.3 Hz, OCH2CH3), 3.69 (2H, bq, J=5.8 Hz, NCH2CH2), 2.70 (2H, t, J=5.8 Hz, NCH2CH2), 1.26 (3H, t, J=7.3 Hz, OCH2CH3); Exact mass (FAB, M+H+) calcd for C20H20N3O6 : 398.1352; Found: 398.1343.

후처리

  1. concentrationconcentrated in vacuo
  2. dissolutionredissolved in 75 mL of tetrahydrofuran
  3. temperatureThe mixture was warmed to ambient temperature for 12 h
  4. customthe tetrahydrofuran was removed in vacuo
  5. customThe residue was partitioned between ethyl acetate and 1N sodium bicarbamate
  6. customthe aqueous phase was separated
  7. extractionextracted with ethyl acetate
  8. washThe combined organics were washed with 1N sodium hydrogen sulfate, water, brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7e7b859a6cf144e391e8fe092c9deabd
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05565449

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