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

HRID 965165

反応式

HRID 965165 の反応式
[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]

参加物

9

反応物 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 10560578HCID 10560578、化合物HCID 676943419-(S)-amino-4-oxa-1,7-diaza-tricyclo[9.6.1.012,17]octadeca-11(18),12,14,16-tetraen-8-one

生成物 1

HCID 15047738Tert-butyl hex-5-enoate

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-08f2c05b10264987a882e8a0deec87c6
出典データセット
uspto-grants-1998_06
特許番号
US05773428

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