4-Methylmorpholine → HCID 68157459、化合物

HRID 242956ノート

反応式

HRID 242956 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([NH2:8])=[CH:6][CH:7]=1.[CH2:16]([O:23][CH2:24][CH2:25][C@H:26]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:27](O)=[O:28])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:34]([O:33][C:31](=[O:32])[NH:30][C@H:26]([C:27](=[O:28])[NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:25][CH2:24][O:23][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:37])([CH3:35])[CH3:36]

参加物

7

反応物 5

HCID 79724-MethylmorpholineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15058464O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserineHCID 214506204-Fluoro-2-phenylaminoaniline

生成物 1

HCID 68157459HCID 68157459、化合物収率 82%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 4-fluoro-N2-phenylbenzene-1,2-diamine (614 mg, 3.04 mmol), (S)-4-benzyloxy-2-tertbutoxycarbonylaminobutyric acid (1.0 g, 3.3 mmol), HOAt (0.450 g, 3.3 mmol), 4-methylmorpholine (0.7 mL, 6.7 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.63 g, 3.3 mmol) in DCM (15 mL) was stirred at RT for 18 h. The reaction mixture was partitioned between DCM and a saturated aqueous solution of NaHCO3. The organic fraction was washed with brine, dried (MgSO4), concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane) to afford the title compound as a yellow oil (1.22 g, 82%). LCMS (Method J): RT 4.17 min [M+H]+ 494.1.

後処理

  1. customThe reaction mixture was partitioned between DCM
  2. washThe organic fraction was washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customthe resulting residue purified by column chromatography (Si—PCC, gradient 0-30% EtOAc in cyclohexane)

出典と根拠

ORDレコード
ord-0fd987af744a45808fffda9515516cc5
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

反応ノート

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