4-Methylmorpholine → Phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(4-{[(phenylmethyl)oxy]carbonyl}phenyl)amino]carbonyl}-1-pyrazolidinecarboxylate

HRID 1396959

反応式

HRID 1396959 の反応式
[CH:1]1([CH2:6][C@H:7]([CH2:28][N:29]([CH:38]=[O:39])[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:8]([N:10]2[C@H:14]([C:15](O)=[O:16])[CH2:13][CH2:12][N:11]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.CN1CCOCC1.F[B-](F)(F)F.COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[NH2:69][C:70]1[CH:85]=[CH:84][C:73]([C:74]([O:76][CH2:77][C:78]2[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=2)=[O:75])=[CH:72][CH:71]=1>C(#N)C>[CH:1]1([CH2:6][C@H:7]([CH2:28][N:29]([CH:38]=[O:39])[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:8]([N:10]2[C@H:14]([C:15]([NH:69][C:70]3[CH:85]=[CH:84][C:73]([C:74]([O:76][CH2:77][C:78]4[CH:83]=[CH:82][CH:81]=[CH:80][CH:79]=4)=[O:75])=[CH:72][CH:71]=3)=[O:16])[CH2:13][CH2:12][N:11]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 98488Benzyl p-aminobenzoateHCID 116312684-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium tetrafluoroborateHCID 86706346HCID 86706346、化合物

生成物 1

HCID 86706391Phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-{[(4-{[(phenylmethyl)oxy]carbonyl}phenyl)amino]carbonyl}-1-pyrazolidinecarboxylate収率 79.2%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid (300 mg, 0.558 mmol) in acetonitrile (10 mL) under N2 at 0° C. was added 4-methylmorpholine (123 mg, 2.2 mmol), followed by 4-[4,6-bis(methyloxy)-1,3,5-triazin-2-yl]-4-methylmorpholin-4-ium tetrafluoroborate (366 mg, 1.116 mmol). The mixture was stirred for 1 h and to this mixture was added phenylmethyl 4-aminobenzoate (191 mg, 0.837 mmol). The mixture was stirred at rt overnight. The mixture was concentrated, and the residue was purified by flash column chromatography eluting with petroleum ether/ethyl acetate (5:1 to 3:1) to provide the title compound (330 mg).

後処理

  1. stirringThe mixture was stirred at rt overnight
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by flash column chromatography
  4. washeluting with petroleum ether/ethyl acetate (5:1 to 3:1)

出典と根拠

ORDレコード
ord-673b094275fd46dbac602e976ca39825
出典データセット
uspto-grants-2014_12
特許番号
US08901119B2

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