Ethyl Acetate → (S)-2-{(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino propionylamino]-3-methylbutyrylamino}-pent-4-enoic acid methyl ester

HRID 2371323

반응식

HRID 2371323 반응식
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C@H:12]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:13]([NH:15][C@@H:16]([CH:20]([CH3:22])[CH3:21])C(O)=O)=[O:14])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].C[N:32]([C:34]([O:38]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)[CH:58]([CH3:60])[CH3:59].C[CH2:65][O:66][C:67]([CH3:69])=[O:68]>CN(C=O)C>[CH3:65][O:66][C:67](=[O:68])[C@@H:69]([NH:32][C:34](=[O:38])[C@@H:16]([NH:15][C:13](=[O:14])[C@@H:12]([NH:23][C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:11][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:1][CH:2]=[CH2:3])=[CH:10][CH:9]=1)[CH:20]([CH3:22])[CH3:21])[CH2:60][CH:58]=[CH2:59]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66847200(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-3-methyl-butyric acid

생성물 1

HCID 66847339(S)-2-{(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino propionylamino]-3-methylbutyrylamino}-pent-4-enoic acid methyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Carboxylic acid 43 (1.00 g, 2.38 mmol), HATU (2.62 mmol) and (S)-allyl-glycine methyl ester hydrochloride (2.62 mmol) were dissolved in DMF (30 mL). DIPEA was added (9.52 mmol) and the reaction mixture was stirred at rt for 18 h before being partitioned between EtOAc and 1M hydrochloric acid. The organic phase was washed sequentially with 1M hydrochloric acid and brine before being dried (MgSO4), filtered and concentrated in vacuo. Purification was achieved using flash chromatography, eluting with a gradient of EtOAc and (50/70) petroleum ether to yield a white solid, 1.05 g, 83%. Rf=0.48 (1/1 EtOAc/(50/70) petroleum ether). m.p. 106-108° C.

후처리

  1. custombefore being partitioned between EtOAc and 1M hydrochloric acid
  2. washThe organic phase was washed sequentially with 1M hydrochloric acid and brine
  3. dry with materialbefore being dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification
  7. washeluting with a gradient of EtOAc and (50/70) petroleum ether
  8. customto yield a white solid, 1.05 g, 83%

출처 및 근거

ORD 기록
ord-b9cdfe73b35543b2b852ce942bf28ead
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08710178B2

연결된 노트

불러오는 중…