4-Methylmorpholine → (-)-methyl(S)-2-[(2-amino-3-nitrobenzoyl)amino]propanoate

HRID 1532444

반응식

HRID 1532444 반응식
[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[OH2:14].ON1[C:20]2C=CC=[N:24][C:19]=2[CH:18]=N1.CN1C[CH2:30][O:29]CC1>O1CCCC1>[NH2:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:24][C@@H:19]([CH3:18])[C:20]([O:29][CH3:30])=[O:14])=[O:6]

참가 물질

5

반응물 3

HCID 79724-MethylmorpholineHCID 2196332-Amino-3-nitrobenzoic acidHCID 701049091-hydroxy-1H-1,2,4-benzotriazole monohydrate

생성물 1

HCID 14879834(-)-methyl(S)-2-[(2-amino-3-nitrobenzoyl)amino]propanoate수율 97.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a stirred and cooled (−12° C.) mixture of 9.10 parts of 2-amino-3-nitrobenzoic acid, 6.95 parts of methyl L-α-alanine monohydrochloride, 13.50 parts of 1-hydroxy-1H-1,2,4-benzotriazole monohydrate and 178 parts of tetrahydrofuran there were added portionwise 5.05 parts of N-methylmorpholine and, after 5 min, 10.3 parts of N,N′-methanetetraylbis[cyclohexanamine] under an argon atmosphere. Stirring was continued for 5½ hours at −12° C. and for 15 hours at room temperature. After cooling to 0° C. for ½ hour, the reaction mixture was filtered and the filtrate was evaporated. The residue was partitioned between ethyl acetate and a saturated sodium hydrogen carbonate solution. The organic layer was separated, washed with NaHCO3 (sat.), dried, filtered and evaporated. The residue was triturated with hexane. The product was filtered off and dried, yielding 13.08 parts (97.9%) of (−)-methyl(S)-2-[(2-amino-3-nitrobenzoyl)amino]propanoate; mp. 132.9° C. (interm. 24).

후처리

  1. temperaturecooled
  2. stirringStirring
  3. waitwas continued for 5½ hours at −12° C. and for 15 hours at room temperature
  4. filtrationthe reaction mixture was filtered
  5. customthe filtrate was evaporated
  6. customThe residue was partitioned between ethyl acetate
  7. customThe organic layer was separated
  8. washwashed with NaHCO3 (sat.)
  9. customdried
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue was triturated with hexane
  13. filtrationThe product was filtered off
  14. customdried

출처 및 근거

ORD 기록
ord-d68b7e8cda6c46e198e00ca9756e68a0
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06201119B1

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