Dimethylformamide → HCID 54145145, compound

HRID 1110265Notes

Reaction equation

HRID 1110265 reaction equation
C1(C[O:8][C:9](=[O:51])[CH2:10][N:11]([C:23]2[CH:28]=[C:27]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:26]=[C:25]([C:48](=[O:50])[NH2:49])[CH:24]=2)[CH2:12][C:13]([O:15]CC2C=CC=CC=2)=[O:14])C=CC=CC=1.[H][H].CN(C=O)C>[Pd].C1COCC1>[C:9]([CH2:10][N:11]([C:23]1[CH:28]=[C:27]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:26]=[C:25]([C:48](=[O:50])[NH2:49])[CH:24]=1)[CH2:12][C:13]([OH:15])=[O:14])([OH:51])=[O:8]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 19388969(3-carbamoyl)-5-(octadecyloxy)phenyl-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 54145145HCID 54145145, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.2 g of N-[(3-carbamoyl)-5-(octadecyloxy)phenyl-N-[2-(phenylmethoxy)-2-oxoethyl]glycine phenylmethyl ester and 0.5 g of 10% palladium on carbon in 100 ml of THF was stirred in a hydrogen atmosphere at room temperature until uptake ceased after 3 hours. DMF (150 ml) was added and the mixture was heated to dissolve the precipitated product. The hot mixture was filtered to remove the catalyst and the filtrate was concentrated at reduced pressure to a solid. Recrystallization from THF gave 1.1 g (69% yield, mp 213°-216°) of N-(carboxymethyl)-N-[(3-carbamoyl)-5-(octadecyloxy)phenyl]glycine.

Workup

  1. temperaturethe mixture was heated
  2. dissolutionto dissolve the precipitated product
  3. filtrationThe hot mixture was filtered
  4. customto remove the catalyst
  5. concentrationthe filtrate was concentrated at reduced pressure to a solid
  6. customRecrystallization from THF

Sources & evidence

ORD record
ord-5ec17cf9e6394c01b9adb89bdad5efa8
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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