4-Methylmorpholine → N-Boc-S-(cyanomethyl)-L-cysteine-L-proline-O-benzyl ester

HRID 1418422

반응식

HRID 1418422 반응식
[C:1]([NH:8][C@H:9]([C:15]([OH:17])=[O:16])[CH2:10][S:11][CH2:12][C:13]#[N:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.C([O:26][C:27](=[O:33])[C@@H:28]1[CH2:32][CH2:31][CH2:30][NH:29]1)C1C=CC=CC=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=2N=N1.[CH3:61]N1CCOCC1>C(#N)C.C(OCC)(=O)C.CN(C=O)C>[N:29]1([CH:61]([O:16][C:15](=[O:17])[C@H:9]([CH2:10][S:11][CH2:12][C:13]#[N:14])[NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:30][CH2:31][CH2:32][C@H:28]1[C:27]([OH:26])=[O:33]

참가 물질

8

반응물 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2733413Proline benzyl ester hydrochlorideHCID 22874698(R)-2-((tert-butoxycarbonyl)amino)-3-((cyanomethyl)thio)propanoic acid

생성물 1

HCID 131720088N-Boc-S-(cyanomethyl)-L-cysteine-L-proline-O-benzyl ester

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

The compound of Example 43 (24.72, 95.06 mmole) and L-proline-O-benzyl ester hydrochloride (22.98 g, 95.06 mmole) are suspended in 140 mL of acetonitrile and 120 mL of DMF at 0° C., then BOP (42.0 g, 95.06 mmole) and NMM (28.84 g, 285.18 mmole) are added. The ice bath is removed after 30 minutes and the reaction is stirred for 18 hours at room temperature. The reaction mixture is reduced in volume under vacuum at 25° C. to give a residue. The residue is taken up in 200 mL ethyl acetate, and is washed successively with 1N hydrochloric acid (1×50 mL) saturated sodium bicarbonate 1×50 mL) and brine (1×50 mL). After drying with MgSO4, the solvent is evaporated under vacuum to give the title compound.

후처리

  1. customThe ice bath is removed after 30 minutes
  2. customis reduced in volume under vacuum at 25° C.
  3. customto give a residue
  4. washis washed successively with 1N hydrochloric acid (1×50 mL) saturated sodium bicarbonate 1×50 mL) and brine (1×50 mL)
  5. dry with materialAfter drying with MgSO4
  6. customthe solvent is evaporated under vacuum

출처 및 근거

ORD 기록
ord-b4162a27c0634a2bbe131739664c8af9
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05883107

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