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

HRID 1815994ノート

反応式

HRID 1815994 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-63d9e70464304b90b3186e55243a83cd
出典データセット
uspto-grants-2005_04
特許番号
US06881736B1

反応ノート

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