(2S)-2-amino-3-hydroxypropanoate → Benzyl O-(O-benzyl-N-benzyloxycarbonyl-L-serinyl)-N-trifluoroacetyl-L-serinate

HRID 2165226노트

반응식

HRID 2165226 반응식
[CH2:1]([O:8][CH2:9][C@@H:10]([C:22]([OH:24])=[O:23])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:25][C:26]([F:44])([F:43])[C:27]([NH:29][C@H:30]([C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])[CH2:31]O)=[O:28].N[C@H](C([O-])=O)CO>C(Cl)Cl.C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][C@@H:10]([C:22]([O:24][CH2:31][C@@H:30]([C:33]([O:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:34])[NH:29][C:27](=[O:28])[C:26]([F:25])([F:43])[F:44])=[O:23])[NH:11][C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 5460791(2S)-2-amino-3-hydroxypropanoateHCID 6993425N-((Phenylmethoxy)carbonyl)-O-(phenylmethyl)-L-serineHCID 14357546benzyl trifluoroacetyl-L-serinate

생성물 1

HCID 18639970Benzyl O-(O-benzyl-N-benzyloxycarbonyl-L-serinyl)-N-trifluoroacetyl-L-serinate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of O-benzyl-N-benzyloxycarbonyl-L-serine (1 g) and benzyl N-trifluoroacetyl-L-serinate (873 mg) in methylene chloride (20 ml) was added N,N-diethylaminopropyl-N'-ethylcarbodiimide hydrochloride (573 mg) and -N,N-dimethylaminopyridine (37 mg) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for an hour at room temperature. The reaction mixture was diluted with ethyl acetate (200 ml) and washed successively with 0.2N hydrochloric acid, water, 10% aqueous sodium hydrogen carbonate, water and brine. After drying over sodium sulfate, the ethyl acetate extract was filtered and concentrated. The residue was chromatographed on silica gel eluting successively with a 1:1 mixture of methylene chloride and hexane, methylene chloride, a 50:1 mixture of methylene chloride and acetone to give benzyl O-(O-benzyl-N-benzyloxycarbonyl-L-serinyl)-N-trifluoroacetyl-I,-serinate (1.5 g).

후처리

  1. customat 0° C
  2. washwashed successively with 0.2N hydrochloric acid, water, 10% aqueous sodium hydrogen carbonate, water and brine
  3. dry with materialAfter drying over sodium sulfate
  4. extractionthe ethyl acetate extract
  5. filtrationwas filtered
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel eluting successively with a 1:1 mixture of methylene chloride and hexane, methylene chloride
  8. additiona 50:1 mixture of methylene chloride and acetone
  9. customto give benzyl O-(O-benzyl-N-benzyloxycarbonyl-L-serinyl)-N-trifluoroacetyl-I

출처 및 근거

ORD 기록
ord-c50d308009c84a0c9750a10fc208d89a
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04939241

반응 노트

불러오는 중…