Dimethylformamide → HCID 54007382, compound

HRID 2118877Notes

Reaction equation

HRID 2118877 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:21]([OH:23])=O)[CH2:10][CH2:11][CH2:12][CH2:13][NH:14][CH:15]([C:17]([O:19][CH3:20])=[O:18])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].ON1C(=O)CCC1=O.C1(N=C=NC2CCCCC2)CCCCC1.CN(C=O)C>C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13][N:14]([CH:15]([C:17]([O:19][CH3:20])=[O:18])[CH3:16])[C:21]1=[O:23])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 86741160HCID 86741160, compound

Product 1

HCID 54007382HCID 54007382, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 4.76 g of the lysine derivative, 1.64 g. of N-hydroxysuccinimide and 3.24 g dicyclohexylcarbodiimide in 250 ml. of DMF. Store this reaction mixture at 0° C. for two days. Concentrate the reaction in vacuo and dissolve the residue in ethyl acetate. Filter and purify the product by silica gel chromatography. Isolate the purified 3-(S)-t-butoxycarbonylamino-1-(1-methoxycarbonylethyl)perhydroazepin-2-one.

Workup

  1. concentrationConcentrate
  2. customthe reaction in vacuo
  3. filtrationFilter
  4. custompurify the product by silica gel chromatography

Sources & evidence

ORD record
ord-21b1485c4a28469abf94607ed5f1db7b
Source dataset
uspto-grants-1987_07
Patent number
US04680392

Reaction notes

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