Tetrahydrofuran → HCID 14837130, compound

Reaction equation

C(OC(NC[C@H]1CC[C@H:13]([C:16]([NH:18][C:19](=[O:29])[C@H:20]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[NH2:21])=O)CC1)=O)(C)(C)C.C(N(CC)CC)C.[Cl:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].[O:43]1CCCC1>>[ClH:37].[NH2:21][C@H:20]([C:19]([NH:18][C@H:16]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:13][OH:43])=[O:29])[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 8471Triethylamine

HCID 10928Ethyl chloroformate

HCID 178453621HCID 178453621, compound

Product 1

HCID 14837130HCID 14837130, compound

Procedure

N-(t-butoxycarbonyl)-3-phenoxy-DL-phenylalanine (I) (7.42 g) obtained in (4) was dissolved in dry tetrahydrofuran (80 ml), triethylamine (3 ml) was added to the solution, and further, ethyl chloroformate (2.40 g) was added under ice-cooling, followed by stirring for 30 minutes. To the solution, 4-acetylanilide (2.70 g) was added and the mixture was stirred under room temperature for 10 hours. To the reaction mixture, ice-water (300 ml) was added, and the crystalline substance precipitated was collected by filtration, thoroughly washed with water, and then dried to obtain N-(t-butoxycarbonyl)-3-phenoxy-DL-phenylalanine 4-acetylanilide (II) 7.07 g) as a white powder. The structure was confirmed by IR and NMR.