4-Methylmorpholine → Tert-butyl hex-5-enoate

HRID 965165

반응식

HRID 965165 반응식
[C:1]([O:5][C:6](=[O:15])[CH2:7][C@@H:8]([CH2:12][CH:13]=[CH2:14])C(O)=O)([CH3:4])([CH3:3])[CH3:2].N[C@H]1CC2=CN(C3C2=CC=CC=3)CCOCCNC1=O.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.CCN=C=NCCCN(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:15])[CH2:7][CH2:8][CH2:12][CH:13]=[CH2:14])([CH3:4])([CH3:3])[CH3:2]

참가 물질

9

반응물 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 10560578HCID 10560578, 화합물HCID 67694341HCID 67694341, 화합물

생성물 1

HCID 15047738Tert-butyl hex-5-enoate

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-(R)-allyl-succinic acid 4-t-butyl ester (5 g, 0.00234 mol), 9-(S)-amino-4-oxa-1,7-diaza-tricyclo[9.6.1.012,17 ]octadeca-11(18),12,14,16-tetraen-8-one (6,38 g, 0.00234mol) in 50 mL DMF added HOBT (3.47 g, 0.026 mol), DMAP (80 mg), N-methylmorpholine (2.84 g, 0.028 mol), and EDCI (6.69 g, 0.035 mol). The mixture was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc (300 mL) and washed with brine (2×100 mL), saturated NaHCO3 (2×100 mL) and brine (1×100 mL), and dried (MgSO4). Removal of the solvents gave 9 g of crude product. Column chromatographic purification (50% EtOAc/CH2Cl2) gave 7.5 g of pure (3R,9S)-3-(8-oxo-4-oxa-1,7-diaza-tricyclo[9.6.1.012,17 ]octadeca-11(18)12,14,16-tetraen-9-yl carbamoyl)-hex-5-enoic acid t-butyl ester, MS: 469(M+).

후처리

  1. washwashed with brine (2×100 mL), saturated NaHCO3 (2×100 mL) and brine (1×100 mL)
  2. dry with materialdried (MgSO4)
  3. customRemoval of the solvents
  4. customgave 9 g of crude product
  5. customColumn chromatographic purification (50% EtOAc/CH2Cl2)

출처 및 근거

ORD 기록
ord-08f2c05b10264987a882e8a0deec87c6
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773428

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