Triethylamine → HCID 131711691, compound

HRID 2052269Notes

Reaction equation

HRID 2052269 reaction equation
[NH2:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:21]([NH2:23])=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7].Cl.[NH:25]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[C@H:26]([C:31](ON1C(=O)CCC1=O)=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29].C(N(CC)CC)C>CN(C=O)C>[NH:25]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[C@H:26]([C:31]([NH:1][C@H:2]([C:11]([NH:13][C@@H:14]([C:21]([NH2:23])=[O:22])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[CH2:3][C:4](=[O:10])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:32])[CH2:27][CH:28]([CH3:30])[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11089751N-[(Phenylmethoxy)carbonyl]-L-leucine 2,5-dioxo-1-pyrrolidinyl esterHCID 131711685HCID 131711685, compound

Product 1

HCID 131711691HCID 131711691, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.0 g (14.0 mmoles) of H-Asp(OtBu)-D-Phg-NH2.HCl, prepared as described in Example 1, Step 4, and 5.13 g (14.2 mmoles) of Z-Leu-OSu are dissolved in 60 ml of DMF, and 1.96 ml (14.0 mmoles) of triethylamine are added to the solution. Next day the reaction mixture is evaporated in vacuo, and the residue is triturated with water. The resulting crude product, weighing 7.32 g, is recrystallized from ethanol under decolourizing. 6.05 g (77.7%) of Z-Leu-Asp(OtBu)-D-Phg-NH2 are obtained; m.p.: 192°-194° C., Rf4 : 0.75. A sample of the product melts as 195°-196° C. after recrystallization from ethanol; [α9 D : -69.5° (c: 1.0, in dimethyl formamide).

Workup

  1. customNext day the reaction mixture is evaporated in vacuo
  2. customthe residue is triturated with water
  3. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-2e3f4c751d6b4e20b69c51ca0a9309cf
Source dataset
uspto-grants-1980_01
Patent number
US04183909

Reaction notes

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