m-Toluidine → alpha-benzyl 4-[N,N-bis(2-chloroethyl)-amino]phenoxycarbonyl-gamma-(3-methylphenyl)-L-glutamine

HRID 861219노트

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HRID 861219 반응식
[CH2:1]([C@@:8]([C:31]([O-:33])=[O:32])([CH2:19][CH:20]([N:24]([CH2:28][CH2:29][Cl:30])[CH2:25][CH2:26][Cl:27])[C:21]([O-:23])=O)[NH:9][C:10]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:36](CC)CC)C.C(OC(Cl)=O)C(C)C.N[C:50]1[CH:55]=[CH:54][CH:53]=[C:52]([CH3:56])[CH:51]=1>O1CCCC1>[CH2:1]([C@@:8]([C:31]([OH:33])=[O:32])([CH2:19][C:20]([N:24]([CH2:25][CH2:26][Cl:27])[CH2:28][CH2:29][Cl:30])([C:50]1[CH:55]=[CH:54][CH:53]=[C:52]([CH3:56])[CH:51]=1)[C:21](=[O:23])[NH2:36])[NH:9][C:10]([O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 7934m-ToluidineHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 86752017HCID 86752017, 화합물

생성물 1

HCID 86752016alpha-benzyl 4-[N,N-bis(2-chloroethyl)-amino]phenoxycarbonyl-gamma-(3-methylphenyl)-L-glutamine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

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온도
25 °C

실험 절차

α-Benzyl4-[N,N-bis(2-chloroethyl)amino]phenoxycarbonyl-L-glutamate (300 mg) in dry tetrahydrofuran (5 ml) was treated with 1.1 equivalents of triethylamine. Isobutylchloroformate (0.08 ml, 1.1 equiv) in dry THF (10 ml) was added slowly to the reaction mixture at -25° C. After 15 minutes, 1.1 equivalents (0.08 ml) m-toluidine in dry tetrahydrofuran (5 ml) was added. The mixture was allowed to warm up to 25° C. and was then continuously stirred for 18 hrs. The reaction mixture was then filtered and the filtrate evaporated to give a residue which was purified by flash column chromatography using mixtures of ethyl acetate/hexane as eluent. Evaporation of appropriate fractions yielded α-benzyl 4-[N,N-bis(2-chloroethyl)amino]phenoxycarbonyl-γ-(3-methylphenyl)-L-glutamine as a white crystalline solid. The NMR data from this product is set out in Table 17.

후처리

  1. filtrationThe reaction mixture was then filtered
  2. customthe filtrate evaporated
  3. customto give a residue which
  4. customwas purified by flash column chromatography
  5. customEvaporation of appropriate fractions

출처 및 근거

ORD 기록
ord-6df02528b8f142f18b095e42036348e7
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05714148

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