Dimethylformamide → HCID 54007382, compound

HRID 1249267Notes

Reaction equation

HRID 1249267 reaction equation
C(O[NH:6][C@H:7]([C:21]([OH:23])=O)[C:8](=C=O)[CH2:9][CH2:10][CH2:11][NH:12][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH3:14])(C)(C)C.ON1C(=O)CC[C:26]1=O.C1(N=C=N[CH:41]2[CH2:46][CH2:45]CCC2)CCCCC1.CN(C=O)C.[C:52]([O:55]CC)(=[O:54])C>>[C:46]([O:55][C:52]([NH:6][C@H:7]1[CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH3:14])[C:21]1=[O:23])=[O:54])([CH3:45])([CH3:41])[CH3:26]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 86741161HCID 86741161, compound

Product 1

HCID 54007382HCID 54007382, compound

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-4fc745f15b1b4c15b89bfd70ecdc8af7
Source dataset
uspto-grants-1986_12
Patent number
US04629787

Reaction notes

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