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

HRID 264009

反応式

HRID 264009 の反応式
[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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

The compound of Example 71 (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.

後処理

  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

出典と根拠

ORDレコード
ord-463914f4a5c546c0ae77221e3510a93c
出典データセット
uspto-grants-1997_07
特許番号
US05646165

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