L-Pyroglutamic Acid → HCID 20706101, compound
Reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([OH:9])=O.ON1C(=O)CCC1=O.C1CCC(N=C=NC2CCCCC2)CC1.[ClH:33].Cl.[S:35]1[CH:39]=[C:38]([CH2:40][C@@H:41]([C:43]([N:45]2[CH2:52][CH2:51][CH2:50][C@H:46]2[C:47]([NH2:49])=[O:48])=[O:44])[NH2:42])[N:37]=[CH:36]1.C(N(CC)CC)C>CN(C)C=O>[ClH:33].[ClH:33].[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:42][C@H:41]([C:43]([N:45]1[CH2:52][CH2:51][CH2:50][C@H:46]1[C:47]([NH2:49])=[O:48])=[O:44])[CH2:40][C:38]1[N:37]=[CH:36][S:35][CH:39]=1)=[O:9]Participants
Procedure
L-Pyroglutamic acid (1.76 g, 13.64 mmol) and N-hydroxysuccinimide (1.73 g, 15 mmol) were dissolved in N,N-dimethylformamide (50 ml). To this solution was added the solution of DCC (3.09 g, 15 mmol) in N,N-dimethylformamide (10 ml) under ice-cooling and the resulting mixture was stirred for 2 h at, the same temperature. 3-(4-thiazolyl)-L-alanyl-L-prolineamide dihydrochloride (4) (6.67 g, 15 mmol) and triethylamine (4.6 ml. 33 mmol) were added successively to the solution and the reaction mixture was stirred overnight. After the precipitation which appeared was filtered off, to the filtrate was added sodium hydrogencarbonate aq. to adjust pH 8. The reaction mixture was subjected to gel filtration column chromatography (MCI gel CHP-20P, 200 ml, aq. MeOH) to give the compound (I-1) (2.54 g, 49%).
Workup
- temperaturecooling
- stirringthe reaction mixture was stirred overnight
- customAfter the precipitation which
- filtrationappeared was filtered off, to the filtrate
- additionwas added sodium hydrogencarbonate aq.
- filtrationThe reaction mixture was subjected to gel filtration column chromatography (MCI gel CHP-20P, 200 ml, aq. MeOH)
- customto give the compound (I-1) (2.54 g, 49%)
Sources & evidence
- ORD record
- ord-94209b2bedff4aaead6e55e573e41213
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06319902B1
Reaction notes
Loading…