1,2-Dichloroethane → Benzyl (3-{2-[methoxy(methyl)amino]-2-oxoethyl}phenyl)carbamate

HRID 1947680노트

반응식

HRID 1947680 반응식
C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.Cl.[CH3:19][NH:20][O:21][CH3:22].C(Cl)CCl.[CH2:27]([O:34][C:35]([NH:37][C:38]1[CH:39]=[C:40]([CH2:44][C:45]([OH:47])=O)[CH:41]=[CH:42][CH:43]=1)=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH3:22][O:21][N:20]([CH3:19])[C:45](=[O:47])[CH2:44][C:40]1[CH:39]=[C:38]([NH:37][C:35](=[O:36])[O:34][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:43]=[CH:42][CH:41]=1

참가 물질

6

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 57907509HCID 57907509, 화합물2회

생성물 1

HCID 57907449Benzyl (3-{2-[methoxy(methyl)amino]-2-oxoethyl}phenyl)carbamate수율 74%

실험 절차

To a suspension of 24.7 g (87 mmol) of (3-{[(benzyloxy)carbonyl]amino}phenyl)acetic acid in 200 mL of dichloromethane (from Step B) was added triethylamine (30.2 mL, 173 mmol) which resulted in some exotherming (+5° C.) and the suspension becoming a solution. After 10 min cooling, HOBt (13.2 g, 87 mmol), N,O-dimethylhydroxylamine HCl (8.5 g, 87 mmol) was added to the solution followed by EDC (16.6 g, 87 mmol) and the resulting mixture stirred at room temperature overnight under nitrogen atmosphere. The solution was transferred to a separatory funnel and washed with 1 M HCl which caused an emulsion. Methanol was added to break up the emulsion and the aqueous was partitioned off. The organics were dried over sodium sulfate, filtered and concentrated under vacuum. Recrystallization of the residue from 1000 mL of 70% hexane in ethyl acetate (heated to reflux and then cooled to room temperature overnight) afforded the title compound (21 g, 74%) as a white solid. LC-MS: m/z (ES) 329 (MH)+.

후처리

  1. customresulted in some exotherming (+5° C.)
  2. temperatureAfter 10 min cooling
  3. customThe solution was transferred to a separatory funnel
  4. washwashed with 1 M HCl which
  5. additionMethanol was added
  6. customthe aqueous was partitioned off
  7. dry with materialThe organics were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customRecrystallization of the residue from 1000 mL of 70% hexane in ethyl acetate (
  11. temperatureheated
  12. temperatureto reflux
  13. temperaturecooled to room temperature overnight)

출처 및 근거

ORD 기록
ord-c32031da9b1349d39c2abeb31d56d48b
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399480B2

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