1,2-Dichloroethane → (+/-)-N-[2-[4-(Triisopropylsilyloxy)benzyl]-3-(carbomethoxy)propionyl]serine benzyl ester
Reaction equation
[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]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
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)+.
Workup
- concentrationAfter 18 hr the mixture was concentrated
- customThe residue was chromatographed on silica gel (80% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-63d9e70464304b90b3186e55243a83cd
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06881736B1
Reaction notes
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