4-Benzyl 1-(2,5-dioxopyrrolidin-1-yl) N-(tert-butoxycarbonyl)-L-aspartate → HCID 131714599, compound

HRID 1380451Notes

Reaction equation

HRID 1380451 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:21]([O:23]N1C(=O)CCC1=O)=O)[CH2:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=[O:7])([CH3:4])[CH3:3].[NH:31](C(OC(C)(C)C)=O)[C@H:32]([C:37]([NH:39][C@H:40]([C:45]([NH:47][NH:48][C:49]([O:51][CH2:52][C:53]([Cl:56])([Cl:55])[Cl:54])=[O:50])=[O:46])[CH2:41][CH2:42][S:43][CH3:44])=[O:38])[C@H:33]([CH2:35][CH3:36])[CH3:34]>C1COCC1.C(OCC)(=O)C>[NH:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@H:9]([C:21]([NH:31][C@H:32]([C:37]([NH:39][C@H:40]([C:45]([NH:47][NH:48][C:49]([O:51][CH2:52][C:53]([Cl:54])([Cl:55])[Cl:56])=[O:50])=[O:46])[CH2:41][CH2:42][S:43][CH3:44])=[O:38])[C@H:33]([CH2:35][CH3:36])[CH3:34])=[O:23])[CH2:10][C:11](=[O:12])[O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 135177984-Benzyl 1-(2,5-dioxopyrrolidin-1-yl) N-(tert-butoxycarbonyl)-L-aspartateHCID 131714600HCID 131714600, compound

Product 1

HCID 131714599HCID 131714599, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The preceding 30 g of oil in solution in 250 ml of THF are treated with 6.4 ml (50 mM) of NEM and 18.9 (45 mM) of Boc-Asp(OBzl)O Su. The apparent pH is adjusted between 6 and 7 by successive additions of NEM. After 4 hours, the product is isolated by evaporation of the THF, take-up in 400 ml of ethyl acetate followed by the same washings as the preceding homologue (3). The residue after drying and evaporation (36.5 g) is purified by chromatography over a column of silica with dichloromethane as solvent containing from 0 to 1.5% of methanol. 25 g (66%) of product presenting an NMR spectrum in accordance with the expected structure are thus obtained.

Workup

  1. customThe residue after drying
  2. customevaporation (36.5 g)
  3. customis purified by chromatography over a column of silica with dichloromethane as solvent
  4. additioncontaining from 0 to 1.5% of methanol
  5. customare thus obtained

Sources & evidence

ORD record
ord-5067ce62be434f8faa7991c30e95de74
Source dataset
uspto-grants-1986_04
Patent number
US04581168

Reaction notes

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