HCID 15051736, compound → HCID 15051737, compound

HRID 1723378Notes

Reaction equation

HRID 1723378 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:38]([O:41][CH3:42])[O:39][CH3:40])[CH:8]=[C:9]2[C:17]=1[CH:16]([CH2:18][O:19][C:20](=[O:22])[NH2:21])[C:15]1([O:24][C:25](=[O:27])[CH3:26])[O:23][N:10]2[CH2:11][CH:12]2[CH:14]1[N:13]2C(OCC1C=CC=CC=1)=O)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:38]([O:39][CH3:40])[O:41][CH3:42])[CH:8]=[C:9]2[C:17]=1[CH:16]([CH2:18][O:19][C:20](=[O:22])[NH2:21])[C:15]1([O:24][C:25](=[O:27])[CH3:26])[O:23][N:10]2[CH2:11][CH:12]2[CH:14]1[NH:13]2)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 15051736HCID 15051736, compound

Product 1

HCID 15051737HCID 15051737, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

11-Benzyloxycarbonyl-8-carbamoyloxymethyl-4-dimethoxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-6,9-diyl diacetate (270 mg) was dissolved in methanol (10 ml). To the solution was added 10% palladium on carbon (300 mg) and the mixture was stirred for 1 hour under hydrogen atmosphere (20 psi) at room temperature. The reaction mixture was filtered through cellulose powder and the filtrate was evaporated in vacuo. The residue was subjected to preparative thin layer chromatography and development was carried out with a mixture of chloroform and methanol to afford 8-carbamoyloxymethyl-4-dimethoxymethyl-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-6,9-diyl diacetate (80 mg).

Workup

  1. filtrationThe reaction mixture was filtered through cellulose powder
  2. customthe filtrate was evaporated in vacuo
  3. additionwas carried out with a mixture of chloroform and methanol

Sources & evidence

ORD record
ord-99dcea53a73640679b2b83822424aa83
Source dataset
uspto-grants-1989_08
Patent number
US04861774

Reaction notes

Loading…