N,N-Dimethyl-1,3-propanediamine → gamma-benzyl-L-glutamic acid Nepsilon-benzyloxycarbonyl-L-lysine
Reaction equation
C([NH:4][C@@H:5]1[C:11](=[O:12])[O:10][C:8](=[O:9])[CH:7]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6]1)(O)=O.CN(C)CCCN.C([NH:30][C@H:31]([C:47]([O:49]C(=O)[C@H](CCCCNC(OCC1C=CC=CC=1)=O)NC(O)=O)=[O:48])[CH2:32][CH2:33][CH2:34][CH2:35][NH:36][C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38])(O)=[O:28]>ClCCCl>[CH2:13]([CH:7]([C:8]([OH:9])=[O:28])[CH2:6][C@@H:5]([C:11]([OH:10])=[O:12])[NH2:4])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1.[CH2:40]([O:39][C:37]([NH:36][CH2:35][CH2:34][CH2:33][CH2:32][C@@H:31]([C:47]([OH:49])=[O:48])[NH2:30])=[O:38])[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To 1,2-dichloroethane (10 ml) was added N-carboxy-γ-benzyl-L-glutamic acid anhydride (1.00 g, 3.80 mmol), and the mixture was cooled to 0° C. N,N-Dimethyl-1,3-propanediamine (0.48 μl, 3.8 μmol) was added as an initiator, and the mixture was stirred at 25° C. for 1 day and cooled again to 0° C. Nα-Carboxy-Nε-benzyloxycarbonyl-L-lysine anhydride (1.16 g, 3.80 mmol) was added, and the mixture was stirred at 25° C. for 3 days to give a γ-benzyl-L-glutamic acid-Nε-benzyloxycarbonyl-L-lysine block copolymer (high molecular weight copolymer). The weight average molecular weight, Mw, of the copolymer was measured by Measurement Method 1 described below. In addition, the composition of the copolymer was measured by Measurement Method 2 described below.
Workup
- temperaturecooled again to 0° C
- stirringthe mixture was stirred at 25° C. for 3 days
Sources & evidence
- ORD record
- ord-75f47b78ea394291bac57610d5878932
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09450174B2
Reaction notes
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