HCID 68161901, compound → HCID 57958910, compound

HRID 1472988Notes

Reaction equation

HRID 1472988 reaction equation
C([O:8][CH2:9][C:10]([O:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([CH2:26][O:27][C:28](=[O:38])[CH2:29][O:30]CC1C=CC=CC=1)=[O:25])=[O:15])=[O:11])C1C=CC=CC=1>CN(C=O)C.[Pd]>[OH:8][CH2:9][C:10]([O:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([CH2:26][O:27][C:28](=[O:38])[CH2:29][OH:30])=[O:25])=[O:15])=[O:11]

Participants

4

Reactant 1

HCID 68161901HCID 68161901, compound

Product 1

HCID 57958910HCID 57958910, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Benzyloxy-acetic acid {6-[2-(2-benzyloxy-acetoxy)-acetyl amino]-hexylcarbamoyl}-methyl ester (250 g) was dissolved in DMF (600 ml) in a pressure vessel (Autoclave), 50% wet palladium on carbon (10%, 75 g) was added and the mixture was stirred under hydrogen atmosphere (8 Kg) for 72 hours at 70° C. The catalyst was removed by filtration and 80% of the DMF was distilled off. The crude product was precipitated by adding to Methanol and filtered and dried to get pure (Hydroxy-acetic acid {6-[2-(2-hydroxy-acetoxy)-acetylamino]-hexylcarbamoyl}-methyl ester) (90 g) as a white powder with a melting point of 156-158° C. The pure product was characterized by 1HNMR (CDCl3+DMSO-d6) δ 1.22 (m, 2H, CH2), 1.38 (m, 2H, CH2), 3.06 (m, 2H, CH2), 4.15 (d, 2H, CH2), 4.48 (s, 2H, CH2), 5.42 (t, 1H, OH), 7.98 (bt, 1H, NH).

Workup

  1. additionwas added
  2. customThe catalyst was removed by filtration and 80% of the DMF
  3. distillationwas distilled off
  4. customThe crude product was precipitated
  5. additionby adding to Methanol
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-de809fdd71124ca5ad6651c5abf8d2bc
Source dataset
uspto-grants-2015_04
Patent number
US09012677B2

Reaction notes

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