Dimethylformamide → Benzyl N-(tert-butoxycarbonyl)-D-alanyl-L-prolinate
Reaction equation
[C:1]([O:5]N[C@@H](C(O)=O)C=C=O)([CH3:4])([CH3:3])[CH3:2].Cl.[NH:15]1[CH2:29][CH2:28][CH2:27][C@H:16]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].O[N:31]1[C:35]2[CH:36]=CC=C[C:34]=2N=N1.CN1C[CH2:45][O:44]CC1.C1(N=C=NC2CCCCC2)CCCCC1.CN(C)C=[O:65]>O1CCCC1>[CH2:20]([O:19][C:17](=[O:18])[C@@H:16]1[CH2:27][CH2:28][CH2:29][N:15]1[C:36](=[O:65])[C@@H:35]([CH3:34])[NH:31][C:45]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:44])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 10.0 g (0.0529 m) of N-tert.-butoxy-carbonyl-D-alanine, 12.75 g (0.0529 m) of L-proline, benzyl ester hydrochloride, 14.28 g (0.0106 m) of 1-hydroxybenzotriazole, 15 ml of N-methylmorpholine and 125 ml of dry tetrahydrofuran together with 10.9 g (0.0529 m) of dicyclohexylcarbodiimide and 15 ml of dry dimethylformamide, reacted and worked up as described above, gave 20.4 g of crude N-tert.-butoxycarbonyl-D-alanyl-L-proline benzyl ester. Removal of the t-boc protective group, as described, gave D-alanyl-L-proline, benzyl ester hydrochloride, m.p. 140°-142°. This material (8.3 g, 0.0265 m) was condensed with 5.92 g (0.0265 m) of N-carbomethoxymethyl-L-prolinehydrochloride as described, to give 3.1 g of syrupy N-carbomethoxyethyl-L-prolyl-D-alanyl-L-proline, benzyl ester. Barium hydroxide treatment of 3.0 g (6.7 mm) of the above diester gave 2.1 g of N-carboxymethyl-L-prolyl-D-alanyl-L-proline; m.p. 145°-148° [α]D25 =-39.9° (C,1, 1:1 CH3OH.H2O).
Workup
- customreacted
Sources & evidence
- ORD record
- ord-8db7a867461547cd98ef8f90a288153c
- Source dataset
- uspto-grants-1984_06
- Patent number
- US04456594
Reaction notes
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