4-Methylmorpholine → HCID 66843294, 화합물

HRID 254044

반응식

HRID 254044 반응식
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:33](=[O:34])[C@H:32]([S:35][CH2:36][C:37]([C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=3)=[O:38])[C@H:31]2[C:46]2[CH:60]=[CH:59][C:49]([O:50][CH2:51][C:52]([NH:54][CH2:55][C:56](O)=[O:57])=[O:53])=[CH:48][CH:47]=2)=[CH:26][CH:25]=1.CN1CCOCC1.[NH2:68][C@@H:69]([C:74]([OH:76])=[O:75])[C:70]([CH3:73])([CH3:72])[CH3:71].[BH4-].[Na+]>C(Cl)Cl.CO>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([N:30]2[C:33](=[O:34])[C@H:32]([S:35][CH2:36][CH:37]([C:39]3[CH:40]=[CH:41][C:42]([Cl:45])=[CH:43][CH:44]=3)[OH:38])[C@H:31]2[C:46]2[CH:47]=[CH:48][C:49]([O:50][CH2:51][C:52]([NH:54][CH2:55][C:56]([NH:68][C@@H:69]([C:74]([OH:76])=[O:75])[C:70]([CH3:73])([CH3:72])[CH3:71])=[O:57])=[O:53])=[CH:59][CH:60]=2)=[CH:28][CH:29]=1

참가 물질

8

반응물 5

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 4311764Sodium borohydrideHCID 6950340D-tert-leucineHCID 66842755HCID 66842755, 화합물

생성물 1

HCID 66843294HCID 66843294, 화합물

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

TBTU (0.020 g, 0.063 mmol) was added to a solution of N-{[4-((2R,3R)-1-(4-chlorophenyl)-3-{[2-(4-chlorophenyl)-2-oxoethyl]thio}-4-oxoazetidin-2-yl)phenoxy]acetyl}glycine (0.030 g, 0.052 mmol) and N-methylmorpholine (0.016 g, 0.157 mmol) in CH2Cl2 (5 ml) at 30° C. After 30 minutes, D-tert-leucine (0.008 g, 0.063 mmol) was added and the mixture was stirred for 30 minutes. The reaction mixture was concentrated. Toluene (2 ml) was added and evaporated. MeOH (3 ml) and sodium borohydride (0.020 g, 0.523 mmol) were added. Full conversion to the corresponding alcohol was obtained after 5 minutes. The reaction was quenched by the addition of 0.1M NH4OAc (1 ml) buffer and the mixture was concentrated. The residue was purified by preparative HPLC using an eluent of 0-50% CH3CN in 0.1M NH4OAc buffer. Freeze-drying of the pure fractions afforded the title compound (0.021 g, 58%) as a colourless solid. 1H NMR [(CD3)2SO), 400 MHz] δ0.85 (s, 9H), 2.82-2.98 (m, 2H), 3.75-3.81 (m, 2H), 3.91-3.96 (m, 1H), 4.29-4.37 (m, 1H), 4.52 (s, 2H), 4.70-4.78 (m, 1H), 5.01-5.06 (m, 1H), 6.97-6.99 (m, 2H), 7.19-7.21 (m, 2H), 7.32-7.36 (m, 8H), 7.52-7.63 (m, 1H), 8.27-8.32 (m, 1H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additionToluene (2 ml) was added
  3. customevaporated

출처 및 근거

ORD 기록
ord-ed6a81a2cdfe4f71a984819335e22d5f
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07871998B2

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