Hydrochloric Acid → HCID 86634316, 화합물

HRID 240231

반응식

HRID 240231 반응식
[NH2:1][C@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].[N+:15]([C:18]1[CH:19]=[C:20]([CH:42]=[C:43]([N+:45]([O-:47])=[O:46])[CH:44]=1)[C:21]([NH:23][C@H:24]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:25][C:26](ON1C(=O)CCC1=O)=[O:27])=[O:22])([O-:17])=[O:16].Cl>O.O1CCCC1>[N+:15]([C:18]1[CH:19]=[C:20]([CH:42]=[C:43]([N+:45]([O-:47])=[O:46])[CH:44]=1)[C:21]([NH:23][C@H:24]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:25][C:26]([NH:1][C@H:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5])=[O:27])=[O:22])([O-:17])=[O:16]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2회HCID 686704(3S)-3-amino-3-phenylpropanoic acidHCID 86634315HCID 86634315, 화합물

생성물 1

HCID 86634316HCID 86634316, 화합물

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

5.65 g of (S)-3-amino-3-phenylpropionic acid were suspended in 70 ml of water, the pH of the suspension was adjusted to 10.5-11 by adding sodium hydroxide solution, and 70 ml of tetrahydrofuran were added. The mixture was cooled to 0-5° C. in an icebath and 13 g of 2,5-dioxopyrrolidin-1-yl(S)-3-(3,5-dinitrobenzamido)-3-phenylpropionate were added in portions with stirring over a period of 15 min. On completion of addition, the pH of the reaction mixture was kept between 9-9.5 by adding sodium hydroxide solution. On attainment of a constant pH with virtually full conversion (HPLC monitoring; <0.5 area % of reactant), the solution was diluted to a volume of about 800 ml with water, a pH of 1.5-2 was established by addling 4 N hydrochloric acid and the mixture was stirred for a further 30 min. The solid was filtered off with suction, washed with water and dried at 50° C. under reduced pressure. The dried solid was digested in 250 ml of tetrahydrofuran at 40° C. for 20 min, the suspension was cooled and the solid (product fraction 1) was filtered off with suction. The mother liquor was concentrated at a water bath temperature of 40° C. to a volume of about 70-80 ml, the resulting suspension was cooled to room temperature, and the solid (product fraction 2) filtered off with suction. The product fractions were combined and dried at 50° C. under reduced pressure. The yield was 11.1 g; HPLC purity >99.5 area %; 1H NMR (DMSO) δ (ppm): 2.64 (d, 2H), 2.77 (m, 2H), 5.15 (m, 1H), 5.52 (m, 1H), 7.10-7.20 (m, 5H), 7.25 (t, 1H), 7.31 (t, 2H), 7.39 (d, 2H), 8.44 (d, 1H), 8.95 (m, 1H), 9.01 (m, 2H), 9.53 (d, 1H), 12.17 (s, 1H, CO2H).

후처리

  1. additionwere added
  2. additionwere added in portions
  3. additionOn completion of addition
  4. stirringthe mixture was stirred for a further 30 min
  5. filtrationThe solid was filtered off with suction
  6. washwashed with water
  7. customdried at 50° C. under reduced pressure
  8. waitThe dried solid was digested in 250 ml of tetrahydrofuran at 40° C. for 20 min
  9. temperaturethe suspension was cooled
  10. filtrationthe solid (product fraction 1) was filtered off with suction
  11. concentrationThe mother liquor was concentrated at a water bath temperature of 40° C. to a volume of about 70-80 ml
  12. filtrationthe solid (product fraction 2) filtered off with suction
  13. customdried at 50° C. under reduced pressure

출처 및 근거

ORD 기록
ord-057c053bc4cf41499772ed6a0a4f2fa7
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08647882B2

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