1,2-Dichloroethane → 3(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-oxo-butyric Acid tert-Butyl Ester Semicarbazone

HRID 1456649ノート

反応式

HRID 1456649 の反応式
[C:1]([O:5][C:6](=[N:29][NH:30][C:31]([NH2:33])=[O:32])[CH2:7][C@H:8]([NH:11]C(OCC1C2CC3C(=CC=CC=3)C=2C=CC=1)=O)[CH:9]=[O:10])([CH3:4])([CH3:3])[CH3:2].C(NCC)C.[C:39]([NH:47][C@@H:48]([CH:63]([CH3:65])[CH3:64])[C:49]([N:51]([CH2:59][C:60]([OH:62])=O)[CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50])(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(#N)C.CCOC(C)=O.O.CN(C=O)C.C(Cl)Cl>[C:1]([O:5][C:6](=[N:29][NH:30][C:31]([NH2:33])=[O:32])[CH2:7][C@H:8]([NH:11][C:60](=[O:62])[CH2:59][N:51]([C:49](=[O:50])[C@@H:48]([NH:47][C:39](=[O:46])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[CH:63]([CH3:64])[CH3:65])[CH2:52][C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)[CH:9]=[O:10])([CH3:4])([CH3:2])[CH3:3]

参加物

11

反応物 5

HCID 111,2-DichloroethaneHCID 8021DiethylamineHCID 757711-HydroxybenzotriazoleHCID 53859725((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetic AcidHCID 566185953(S)-(1-fluorenylmethyloxycarbonylamino)-4-oxobutyric acid tert-butyl ester semicarbazone

生成物 1

HCID 545745803(S)-(2-((2(S)-Benzoylamino-3-methylbutyryl)benzylamino)acetylamino)-4-oxo-butyric Acid tert-Butyl Ester Semicarbazone

試薬・触媒・溶媒 5

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 3(S)-(1-fluorenylmethyloxycarbonylamino)-4-oxobutyric acid tert-butyl ester semicarbazone (678 mg, 1.5 mmol; Prepared in a similar manner to the benzyloxycarbonyl analog in Graybill et al., Int. J. Protein Res. , 44, pp. 173-82 (1994)) in acetonitrile (5.0 mL) was added diethylamine (780 μL, 7.5 mmol) and the reaction allowed to stir at rt for 1 hr. The reaction was concentrated in vacuo and the residue co-concentrated with toluene (3×) in vacuo. To a suspension of the residue, compound 704 (555 mg, 1.5 mmol) and HOBT (224 mg, 1.66 mmol) in 1:1 CH2Cl2 :DMF (10 mL) at 0° C., was added EDC (318 mg, 1.66 mmol). The reaction was warmed to rt and stirred over night. The reaction was diluted with EtOAc and H2O. The layers were separated and the organic phase washed with sat. aq. NaHCO3, sat. aq. KHSO4, brine, dried over MgSO4, filtered and concentrated in vacuo. Chromatography of the residue on silica gel (elution with 2-6% MeOH:CH2Cl2) provided 600 mg of compound 705. ##STR84##

後処理

  1. concentrationThe reaction was concentrated in vacuo
  2. temperatureThe reaction was warmed to rt
  3. stirringstirred over night
  4. customThe layers were separated
  5. washthe organic phase washed with sat. aq. NaHCO3, sat. aq. KHSO4, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-72025e5cced5432db4183b6fd4b8f560
出典データセット
uspto-grants-1998_12
特許番号
US05843904

反応ノート

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