1,2-Dichloroethane → (+/-)-N-[2-[4-(Triisopropylsilyloxy)benzyl]-3-(carbomethoxy)propionyl]serine benzyl ester

HRID 1815994노트

반응식

HRID 1815994 반응식
[C:1]([CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])=[CH:13][CH:12]=1)[CH2:5][C:6]([O:8][CH3:9])=[O:7])(O)=[O:2].Cl.[CH2:29]([O:36][C:37](=[O:42])[C@H:38]([CH2:40][OH:41])[NH2:39])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.C(Cl)CCl>CN(C=O)C>[CH2:29]([O:36][C:37](=[O:42])[C@H:38]([CH2:40][OH:41])[NH:39][C:1](=[O:2])[CH:4]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][Si:18]([CH:19]([CH3:21])[CH3:20])([CH:25]([CH3:26])[CH3:27])[CH:22]([CH3:24])[CH3:23])=[CH:15][CH:16]=1)[CH2:5][C:6]([O:8][CH3:9])=[O:7])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 12930233Benzyl L-serinate--hydrogen chloride (1/1)HCID 20775649Methyl (+/-)-3-carboxy-4-[4-(triisopropylsilyloxy)phenyl]butanoate

생성물 1

HCID 20775644(+/-)-N-[2-[4-(Triisopropylsilyloxy)benzyl]-3-(carbomethoxy)propionyl]serine benzyl ester수율 79%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of methyl (±)-3-carboxy-4-[4-(triisopropylsilyloxy)phenyl]butanoate (5.00 g, 12.67 mmole) in dry DMF (60 mL) at RT was added serine benzyl ester hydrochloride (3.52 g, 15.21 mmole), HOBt (2.06 g, 15.21 mmole), Et3N (5.3 mL, 38.01 mmole), and EDC (2.92 g, 15.21 mmole). After 18 hr the mixture was concentrated. The residue was chromatographed on silica gel (80% EtOAc/hexanes) to give the title compound (5.76 mg, 79%) as a pale yellow oil: MS (ES) m/e 572 (M+H)+.

후처리

  1. concentrationAfter 18 hr the mixture was concentrated
  2. customThe residue was chromatographed on silica gel (80% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-63d9e70464304b90b3186e55243a83cd
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06881736B1

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