Boc-D-homophenylalanine → N-Boc-D-homophenylalanine L-serine Benzyl Ester

HRID 1532782Notes

Reaction equation

HRID 1532782 reaction equation
[C:1]([NH:8][C@@H:9]([C:18]([OH:20])=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.[CH2:22]([O:29][C:30](=[O:35])[C@H:31]([CH2:33][OH:34])[NH2:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:1]([NH:8][C@@H:9]([C:18]([OH:20])=[O:19])[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2].[CH2:22]([O:29][C:30](=[O:35])[C@H:31]([CH2:33][OH:34])[NH2:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 2755954Boc-D-homophenylalanineHCID 12930233Benzyl L-serinate--hydrogen chloride (1/1)

Product 1

HCID 131722456N-Boc-D-homophenylalanine L-serine Benzyl EsterYield 34.1%

Procedure

This compound was prepared from N-Boc-D-homophenylalanine (500 mg) and L-serine benzyl ester hydrochloride (415 mg), with purification by chromatography over silica gel (40% ethyl acetate/hexane) to afford title compound (290 mg) as a glassy solid: 1H NMR (400 Mz, CDCl3) δ1.42 (s, 9H), 1.97 (m, 1H), 2.18 (m, 1H), 2.70 (m, 2H), 3.98 (m, 2H), 4.19 (m, 1H), 4.64 (m, 1H), 5.29 (bs, 2H), 7.16-7.29 (m, 5H), and 7.36 (bs, 5H).

Sources & evidence

ORD record
ord-ae78a53c14954357aefadabd9a6f1ba6
Source dataset
uspto-grants-2001_03
Patent number
US06204279B1

Reaction notes

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